Yaozh News Star Club Edu TOP100 Customer Service APP
Iphone Download Android Download
  • English
  • 简体中文
Login Register
Search
Current Location： Home > Feedback Help Print

【结 构 式】

【分子编号】10467

【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate

【CA登记号】32981-86-5

【 分 子 式 】C29H36O10

【 分 子 量 】544.59884

【元素组成】C 63.96% H 6.66% O 29.38%
与该中间体有关的原料药合成路线共 15 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9合成路线10合成路线11合成路线12合成路线13合成路线14合成路线15

合成路线1

该中间体在本合成路线中的序号：(XIII)

A new partial synthesis for taxol has been reported: The cyclization of N-(4-methoxyphenyl)benzylideneimine (I) with acetoxyacetyl chloride (II) by means of triethylamine in dichloromethane gives cis-3-acetoxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one (III), which is treated with ceric ammonium nitrate in acetonitrile to afford cis-3-acetoxy-4-phenylazetidin-2-one (IV). Hydrolysis of (IV) with KOH in THF-water yields cis-3-hydroxy-4-phenylazetidin-2-one (V), which is submitted to optical resolution giving the (3R,4S)-isomer (VI). The reaction of (VI) with ethyl vinyl ether (VII) by means of methanesulfonic acid in THF affords (3R,4S)-3-(1-ethoxyethoxy)-4-phenylazetidin-2-one (VIII), which is benzoylated with benzoyl chloride (IX) and butyllithium in hexane to give (X). Opening of the azetidine ring of (X) with KOH in THF-water gives (2R,3S)-3-(benzamido)-2-(1-ethoxyethoxy)propanoic acid (XI), which is cyclized with potassium tert-butoxide and methanesulfonyl chloride to (4S,5R)-5-(1-ethoxyethoxy)-2,4-diphenyl-5,6-dihydro-4H-1,3-oxazin-6-one (XII). Finally, this compound is condensed with 7-O-(triethylsilyl)baccatin III (XIV) [prepared from 10-deacetylbaccatin III (XIII) by successive reaction with triethylsilyl chloride and acetyl chloride] by means of dimethylaminopyridine (DMAP) in pyridine.

参考文献 中间体
合成目标
【1】 Holton, R.A. (University of Florida); Method for preparation of taxol using an oxazinone. US 5015744 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10455 N-(4-Methoxyphenyl)-N-[(Z)-benzylidene]amine; 4-Methoxy-N-[(Z)-benzylidene]aniline 783-08-4 C14H13NO 详情 详情
(II) 10456 Acetoxiacetil chloride; 2-chloro-2-oxoethyl acetate 13831-31-7 C4H5ClO3 详情 详情
(III) 10457 (3R,4S)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetanyl acetate C18H17NO4 详情 详情
(IV) 10458 (3R,4S)-2-oxo-4-phenylazetanyl acetate C11H11NO3 详情 详情
(V) 63030 cis-3-Hydroxy-4-phenyl-2-azetanone; (3R*,4S*)-3-Hydroxy-4-phenyl-2-azetanone C9H9NO2 详情 详情
(VI) 10459 (3R,4S)-3-Hydroxy-4-phenyl-2-azetanone C9H9NO2 详情 详情
(VII) 18762 1-Ethoxyethylene; Ethyl vinyl ether；Ethoxyethene 109-92-2 C4H8O 详情 详情
(VIII) 10462 (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetanone C13H17NO3 详情 详情
(IX) 10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
(X) 10464 (3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetanone C20H21NO4 详情 详情
(XI) 10465 (2R,3S)-3-(Benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropionic acid C20H23NO5 详情 详情
(XII) 10466 (4S,5R)-5-(1-Ethoxyethoxy)-2,4-diphenyl-4,5-dihydro-6H-1,3-oxazin-6-one C20H21NO4 详情 详情
(XIII) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(XIV) 10468 (1S,2S,3R,4S,7R,9R,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情

合成路线2

该中间体在本合成路线中的序号：(I)

1) The selective protection of 10-deacetylbaccatin III (I) with triethylsilyl chloride (TESCl) gives the monosilylated compound (II), which is acetylated with acetic anhydride and pyridine to yield baccatin III (III). The condensation of (III) with (2R,3S)-3-benzamido-2-(1-ethoxyethoxy)-3-phenylpropionic acid (IV) by means of di-2-pyridyl carbonate (DPC) and dimethylaminopyridine (DMAP) affords protected paclitaxel (V), which is finally deprotected with HCl in ethanol/water. (Denis, J.-N. and Greene, A.E. J Amer Chem Soc 1988, 110: 5917).

参考文献 中间体
合成目标
【1】 Guy, R.K.; Nicolaou, K.C.; Dai, W.M.; Chemistry and biology of taxol. Angew Chem. Int Ed Engl 1994, 33, 1, 15.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 10537 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(III) 10473 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情
(IV) 10465 (2R,3S)-3-(Benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropionic acid C20H23NO5 详情 详情
(V) 10540 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C57H73NO15Si 详情 详情

合成路线3

该中间体在本合成路线中的序号：(XI)

A partial synthesis of Taxol starting from deacetyl Baccatin III (XI) has been developed: The starting compounds, the acid (I) and the silylated Baccatin III (II) have been obtained as follows: a) The reaction of 3(S)-amino-2(R)-hydroxy-3-phenylpropionic acid ethyl ester (VIII) with benzyloxycarbonyl chloride and Na2CO3 in ethyl or tert-butyl ether/water gives 3(S)-(benzyloxycarbonylamino)-2(R)-hydroxy-3-phenylpropionic acid ethyl ester (IX), which is condensed with benzyloxymethyl chloride by means of BuLi in THF yielding the fully protected ester (X). The hydrolysis of (X) with LiOH in ethanol/water affords the desired acid (I). b) The silylation of (deacetyl Baccatin III) (XI) with triethylsilyl chloride in pyridine gives the monosilylated deacetyl Baccatin III (XII), which is then acetylated with acetyl chloride in pyridine or BuLi in THF to afford the desired silylated Baccatin III (II).

参考文献 中间体
合成目标
【1】 Sisti, N.J.; Swindell, C.S.; Chander, M.C. (NaPro BioTherapeutics, Inc.); Paclitaxel synthesis from precursor compounds and methods of producing the same. US 5675025 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10736 (2R,3S)-3-[[(Benzyloxy)carbonyl]amino]-2-[(benzyloxy)methoxy]-3-phenylpropionic acid C25H25NO6 详情 详情
(II) 10737 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-9-methoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C32H40O11 详情 详情
(III) 10738 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-[(benzyloxy)methoxy]-3-phenylpropanoyl]oxy)-1-hydroxy-9-methoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C57H63NO16 详情 详情
(IV) 10739 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-amino-2-[(benzyloxy)methoxy]-3-phenylpropanoyl]oxy)-1-hydroxy-9-methoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C49H57NO14 详情 详情
(VIII) 10548 ethyl (2R,3S)-3-amino-2-hydroxy-3-phenylpropanoate C11H15NO3 详情 详情
(IX) 10741 ethyl (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-3-phenylpropanoate C19H21NO5 详情 详情
(X) 10742 ethyl (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-[(benzyloxy)methoxy]-3-phenylpropanoate C27H29NO6 详情 详情
(XI) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(XII) 10744 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情

合成路线4

该中间体在本合成路线中的序号：(I)

A novel semisynthetic method for the production of paclitaxel from 10-deacetylbaccantin-III using dialkyldichlorosilanes has been reported: The protection of the 7-OH of 10-deacetylbaccatin-III (I) by reaction first with dichlorodiethylsilane (II) and imidazole and then with methanol gives 7-O-[diethyl(methoxy)silyl]baccatin-III (III), which is regioselectively acetylated at the 10-OH with acetylimidazole and LiHMDS to yield the acetate (IV). The esterification of (IV) with the chiral oxazolinecarboxylic acid (V) by means of LiHMDS affords the corresponding ester (VI), which is treated with TFA in HOAc/water in order to perform desilylation and open the oxazoline ring to furnish paclitaxel. Other silylating agents, such as dimethyldichlorosilane, dipropyldichlorosilane, diisopropyldichlorosilane, dibutyldichlorosilane and diphenyldichlorosilane, and other alcohols, such as EtOH, PrOH, i-PrOH, t-BuOH, 3,3,3-trifluoroethanol and others, can also be used in the silylation step.

参考文献 中间体
合成目标
【1】 Dillon, J.L. Jr.; Vemishetti, P.; Gibson, F.S. (Bristol-Myers Squibb Co.); Semi-synthesis of paclitaxel using dialkyldichlorosilanes. WO 0073293 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 43822 dichloro(diethyl)silane 1719-53-5 C4H10Cl2Si 详情 详情
(III) 43823 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-9-[[diethyl(methoxy)silyl]oxy]-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C34H48O11Si 详情 详情
(IV) 43824 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-9-[[diethyl(methoxy)silyl]oxy]-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C36H50O12Si 详情 详情
(V) 10597 (4S,5R)-2,4-Diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylic acid C16H13NO3 详情 详情
(VI) 43825 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-9-[[diethyl(methoxy)silyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carb C52H61NO14Si 详情 详情

合成路线5

该中间体在本合成路线中的序号：(I)

The acylation of 10-deacetylbaccatin III (I) with CDI in chloroform gives the 7,10-bis-O-(imidazolylcarbonyl) derivative (II), which is condensed with the chiral oxazolidinecarboxylic acid (III) by means of DCC and DMAP in hot toluene to yield the corresponding ester (IV). The hydrolysis of (IV) with aqueous TFA affords compound (V), which is finally treated with (Boc)2O and NaHCO3 in THF to provide the target docetaxel.

参考文献 中间体
合成目标
【1】 Duvvuri, S.; Puranik, R. (Dr. Reddy's Research Foundation); An improved process for the preparation of docetaxel. WO 0212216 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 54926 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1,15-dihydroxy-9-[(1H-imidazol-1-ylcarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-12-yl 1H-imidazole-1-carboxylate C37H40N4O12 详情 详情
(III) 10551 (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolane-5-carboxylic acid C17H23NO5 详情 详情
(IV) 54927 5-{(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1-hydroxy-9,12-bis[(1H-imidazol-1-ylcarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl} 3-(tert-butyl) (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate C54H61N5O16 详情 详情
(V) 12497 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C38H45NO12 详情 详情

合成路线6

该中间体在本合成路线中的序号：(VII)

The C-7 hydroxyl group of 10-deacetyl baccatin III (VII) was selectively protected with triethylsilyl chloride and imidazole to yield silyl ether (VIII). Subsequent selective acylation of (VIII) at C-10 hydroxyl group with propionyl chloride in the presence of LiN(SiMe3)2 afforded ester (IX). The title taxoid was then obtained by further coupling with b-lactam (VI) using LiN(SiMe3)2 in THF at low temperature, followed by desilylation with HF in pyridine.

参考文献 中间体
合成目标
【1】 Lin, S.; et al.; Syntheses and biological activity of advanced second-generation taxoids. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 315.
【2】 Takahashi, N.; et al.; Growth inhibition of gastric cancer cells by troglitazone, a ligand for peroxisome proliferator-activated receptor. Dig Dis Week (May 16 1999, Orlando) 1999, Abst 3684.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 19157 tert-butyl (2S,3R)-2-(2-methyl-1-propenyl)-4-oxo-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate C21H39NO4Si 详情 详情
(VII) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(VIII) 21737 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(IX) 10473 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情

合成路线7

该中间体在本合成路线中的序号：(VIII)

The C-7 hydroxyl group of 10-deacetyl baccatin III (VIII) was selectively protected with triethylsilyl chloride and imidazole to yield silyl ether (IX). Subsequent selective acetylation of (IX) at C-10 hydroxyl group with acetyl chloride in the presence of LiN(SiMe3)2 afforded ester (X). The title taxoid was then obtained by further coupling of (X) with b-lactam (VII) using LiN(SiMe3)2 in THF at low temperature, followed by desilylation with HF in pyridine.

参考文献 中间体
合成目标
【1】 Lin, S.; et al.; Syntheses and biological activity of advanced second-generation taxoids. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 315.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 21743 tert-butyl (2S,3R)-2-[(1S)-2,2-dimethylcyclopropyl]-4-oxo-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate C22H41NO4Si 详情 详情
(VIII) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(IX) 21737 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(X) 10473 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情

合成路线8

该中间体在本合成路线中的序号：(VIII)

The C-7 hydroxyl group of 10-deacetyl baccatin III (VIII) was selectively protected with triethylsilyl chloride and imidazole to yield silyl ether (IX). Subsequent selective acylation of (IX) at C-10 hydroxyl group with cyclopropanecarbonyl chloride (X) in the presence of LiN(SiMe3)2 afforded ester (XI). The title taxoid was then obtained by further coupling of (XI) with b-lactam (VII) using LiN(SiMe3)2 in THF at low temperature, followed by desilylation with HF in pyridine.

参考文献 中间体
合成目标
【1】 Lin, S.; et al.; Syntheses and biological activity of advanced second-generation taxoids. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 315.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 21735 tert-butyl (2R,3R)-2-(difluoromethyl)-4-oxo-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate C18H33F2NO4Si 详情 详情
(VIII) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(IX) 21737 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(X) 14061 Cyclopropanecarbonyl chloride; Cyclopropanecarboxylic acid chloride 4023-34-1 C4H5ClO 详情 详情
(XI) 21783 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-12-[(cyclopropylcarbonyl)oxy]-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C39H54O11Si 详情 详情

合成路线9

该中间体在本合成路线中的序号：(VIII)

The C-7 hydroxyl group of 10-deacetyl baccatin III (VIII) was selectively protected with triethylsilyl chloride and imidazole to yield silyl ether (IX). Subsequent selective acylation of (IX) at C-10 hydroxyl group with acid chloride (X) in the presence of LiN(SiMe3)2 afforded ester (XI). The title taxoid was then obtained by further coupling of (XI) with b-lactam (VII) using LiN(SiMe3)2 in THF at low temperature, followed by desilylation with HF in pyridine

参考文献 中间体
合成目标
【1】 Lin, S.; et al.; Syntheses and biological activity of advanced second-generation taxoids. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 315.
【2】 Ferlini, C.; Scambia, G.; Lin, S.; Bernacki, R.J.; Ojima, I.; Wang, T.; Pera, P.; Slater, J.C.; Syntheses and biological activity of C3'-difluoromethyl taxoids. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 39.
【3】 Pera, P.; Scambia, G.; Ojima, I.; Lin, S.; Wang, T.; Ferlini, C.; Slater, J.C.; Bernacki, R.J.; Syntheses and biological activity of C-3'-difluoromethyl-taxoids. Bioorg Med Chem Lett 2000, 8, 7, 1619.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 21735 tert-butyl (2R,3R)-2-(difluoromethyl)-4-oxo-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate C18H33F2NO4Si 详情 详情
(VIII) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(IX) 21737 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(X) 21738 3,3-dimethylbutanoyl chloride 7065-46-5 C6H11ClO 详情 详情
(XI) 21739 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-12-[(3,3-dimethylbutanoyl)oxy]-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C41H60O11Si 详情 详情

合成路线10

该中间体在本合成路线中的序号：(I)

The reaction of 10-O-deacetyl-baccatin III (I) with triethylsilyl chloride and pyridine gives the 7-O-silyl derivative (II), which is acylated with Ac2O and pyridine to yield 7-O-(triethylsilyl)baccatin III (III). The condensation of (III) with the chiral oxazolidine-carboxylic acid (IV) by means of DCC and DMAP in ethyl acetate affords the 13-O-ester (V), which is desilylated by means of HF and TEA in dichloromethane to provide the free 7-hydroxy derivative (VI). The reaction of (VI) with dimethylsulfoxide, Ac2O and HOAc gives the 7-O-(methylsulfanylmethyl) derivative (VII), which is finally hydrolyzed at the oxazolidine ring by means of HCl in ethyl acetate to give rise to the target 7-O-(methlsulfanylmethyl)taxol.

参考文献 中间体
合成目标
【1】 Bourzat, J.-D.; Commercon, A.; Ojima, I.; Bouchard, H. (Aventis Pharma SA; State University of New York, Albany); Methods for preparing new taxoids and pharmaceutical compsns. containing them. WO 0270498 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 10537 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(III) 10473 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情
(IV) 57902 (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid C24H21NO5 详情 详情
(V) 57903 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate C61H71NO15Si 详情 详情
(VI) 57904 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate C55H57NO15 详情 详情
(VII) 57905 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-9-[(methylsulfanyl)methoxy]-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate C57H61NO15S 详情 详情

合成路线11

该中间体在本合成路线中的序号：(I)

The reaction of 10-O-deacetyl-baccatin III (I) with triethylsilyl chloride and pyridine gives the 7-O-silyl derivative (II), which is acylated with Ac2O and pyridine to yield 7-O-(triethylsilyl)baccatin III (III). The desilylation of (III) by means of HCl in ethanol yields baccatin III (VIII), which is condensed with DMSO by means of Ac2O and HOAc to afford the ketonic derivative (IX). The reduction of (IX) by means of NaBH4 in ethanol affords 7-O-(methylsulfanylmethyl)baccatin III (X), which is condensed with the chiral azetidinone (XI) by means of LiHMDS in THF to provide 2'-O-(1-ethoxyethyl)-7-O-(methylsulfanylmethyl)taxol (XII). Finally, this compound is deprotected by means of HCl in ethanol to give the target 7-O-(methylsulfanylmethyl)taxol.

参考文献 中间体
合成目标
【1】 Bourzat, J.-D.; Commercon, A.; Ojima, I.; Bouchard, H. (Aventis Pharma SA; State University of New York, Albany); Methods for preparing new taxoids and pharmaceutical compsns. containing them. WO 0270498 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 10537 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(III) 10473 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情
(VIII) 10447 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C31H38O11 详情 详情
(IX) 57906 (1S,2S,3R,4S,7R,9S,10S,12R)-4,12-bis(acetyloxy)-1-hydroxy-10,14,17,17-tetramethyl-9-[(methylsulfanyl)methoxy]-11,15-dioxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C33H40O11S 详情 详情
(X) 57907 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-9-[(methylsulfanyl)methoxy]-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C33H42O11S 详情 详情
(XI) 10464 (3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetanone C20H21NO4 详情 详情
(XII) 57908 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-9-[(methylsulfanyl)methoxy]-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C53H63NO15S 详情 详情

合成路线12

该中间体在本合成路线中的序号：(I)

The reaction of 10-O-deacetyl-baccatin III (I) with triethylsilyl chloride and pyridine gives the 7-O-silyl derivative (II), which is acylated with Ac2O and pyridine to yield 7-O-(triethylsilyl)baccatin III (III). The condensation of (III) with the chiral azetidine (XI) by means of LiHMDS In THF affords 2'-O-(1-ethoxyethyl)-7-O-(triethylsilyl)taxol (XIII), which is treated with HF and pyridine to provide the desilylated taxol derivative (XIV). The reaction of (XIV) with DMSO, Ac2O and HOAc gives the 2'-O-protected 7-O-(methylsulfanylmethyl) derivative (XII), which is finally deprotected by means of HCl in ethanol to yield the target 7-O-(methylsulfanylmethyl)taxol.

参考文献 中间体
合成目标
【1】 Bourzat, J.-D.; Commercon, A.; Ojima, I.; Bouchard, H. (Aventis Pharma SA; State University of New York, Albany); Methods for preparing new taxoids and pharmaceutical compsns. containing them. WO 0270498 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 10537 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C35H50O10Si 详情 详情
(III) 10473 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C37H52O11Si 详情 详情
(XI) 10464 (3R,4S)-1-Benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetanone C20H21NO4 详情 详情
(XII) 57908 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-15-{[(2R,3S)-3-(benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy}-1-hydroxy-10,14,17,17-tetramethyl-9-[(methylsulfanyl)methoxy]-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C53H63NO15S 详情 详情
(XIII) 10505 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C57H73NO15Si 详情 详情
(XIV) 10540 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-(1-ethoxyethoxy)-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C57H73NO15Si 详情 详情

合成路线13

该中间体在本合成路线中的序号：(XIV)

10-Deacetylbaccatin III (XIV) was protected by treatment with triethylsilyl chloride and imidazole, and the resulting trisilylated compound (XV) was debenzoylated to diol (XVI) by using Red-Al(R). Selective coupling of (XVI) with m-anisic acid (XVII) yielded the m-methoxybenzoate ester (XVIII). Complete desilylation of (XVIII) with HF-pyridine, followed by selective resilylation at C-7, furnished (XIX). The 10-hydroxyl group was then selectively acylated with p-methoxyphenylacetyl chloride (XX) to afford ester (XXI). Finally, coupling of the modified baccatin (XXI) with the intermediate lactam (XIII) in the presence of lithium hexamethyldisilazide, and then deprotection with HF-pyridine, gave rise to the desired taxoid.

参考文献 中间体
合成目标
【1】 Strum, M.; Tynebor, R.; Pera, P.; Bernacki, R.J.; Ojima, I.; Synthesis and SAR of advanced second generation taxoids. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 132.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 19157 tert-butyl (2S,3R)-2-(2-methyl-1-propenyl)-4-oxo-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate C21H39NO4Si 详情 详情
(XIV) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(XV) 51201 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C47H78O10Si3 详情 详情
(XVI) 51202 (1S,2S,3R,7R,9S,10S,12R,15S)-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-4-yl acetate C40H74O9Si3 详情 详情
(XVII) 28559 m-Anisic acid; 3-Methoxybenzoic acid 586-38-9 C8H8O3 详情 详情
(XVIII) 51203 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C48H80O11Si3 详情 详情
(XIX) 51204 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C36H52O11Si 详情 详情
(XX) 26758 2-(4-methoxyphenyl)acetyl chloride 4693-91-8 C9H9ClO2 详情 详情
(XXI) 51213 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,15-dihydroxy-12-[[2-(4-methoxyphenyl)acetyl]oxy]-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C45H60O13Si 详情 详情

合成路线14

该中间体在本合成路线中的序号：(I)

10-Deacetylbaccatin III (I) was protected by treatment with triethylsilyl chloride and imidazole, and the resulting trisilylated compound (II) was debenzoylated to diol (III) by using Red-Al(R). Coupling of (III) with m-anisic acid (IV) yielded the m-methoxybenzoate ester (V). Complete desilylation of (V), followed by selective resilylation at C-7 with triethylsilyl chloride, furnished (VI). Acylation at C-10 and C-13 by means of Ac2O and DMAP, followed by desilylation, gave the modified baccatin (VII).

参考文献 中间体
合成目标
【1】 Strum, M.; et al.; Synthesis and SAR of new taxane reversal agents. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 131.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 51201 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C47H78O10Si3 详情 详情
(III) 51202 (1S,2S,3R,7R,9S,10S,12R,15S)-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-4-yl acetate C40H74O9Si3 详情 详情
(IV) 28559 m-Anisic acid; 3-Methoxybenzoic acid 586-38-9 C8H8O3 详情 详情
(V) 51203 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12,15-tris[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C48H80O11Si3 详情 详情
(VI) 51204 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C36H52O11Si 详情 详情
(VII) 51205 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12,15-tris(acetoxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl 3-methoxybenzoate C34H42O13 详情 详情

合成路线15

该中间体在本合成路线中的序号：(I)

Oxidation of 10-deacetylbaccatin III (I) by means of cupric acetate yielded diketone (II), in equilibrium with the retroaldol product (III). Subsequent reduction employing NaBH4 and CeCl3 produced the seco-taxane (IV) as the major reaction product. Selective protection of the 7 and 9 hydroxyl groups was achieved by treatment with chlorotriethylsilane and imidazole. The resultant 7,9-disilylated derivative (V) was then acylated by the oxazolidinecarboxylic acid (VI) to furnish, after acidic hydrolysis, the title C-seco taxane derivative.

参考文献 中间体
合成目标
【1】 Appendino, G.; et al.; Synthesis and evaluation of C-seco paclitaxel analogues. Tetrahedron Lett 1997, 38, 24, 4273.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10467 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 32981-86-5 C29H36O10 详情 详情
(II) 54790 (1S,2S,3R,4S,7R,10S,15S)-4-(acetyloxy)-1,9,15-trihydroxy-10,14,17,17-tetramethyl-11,12-dioxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-2-yl benzoate C29H34O10 详情 详情
(III) 54791 (1S,2S,3R,9S)-3-[(2R,3S)-3-(acetyloxy)-2-(2-oxoethyl)oxetanyl]-1,5,9-trihydroxy-4,8,11,11-tetramethyl-6-oxobicyclo[5.3.1]undeca-4,7-dien-2-yl benzoate C29H34O10 详情 详情
(IV) 54792 (1S,2S,3R,9S)-3-[(2R,3S)-3-(acetyloxy)-2-(2-hydroxyethyl)oxetanyl]-1,5,9-trihydroxy-4,8,11,11-tetramethyl-6-oxobicyclo[5.3.1]undeca-4,7-dien-2-yl benzoate C29H36O10 详情 详情
(V) 54793 (1S,2S,3R,9S)-3-((2R,3S)-3-(acetyloxy)-2-{2-[(triethylsilyl)oxy]ethyl}oxetanyl)-1,9-dihydroxy-4,8,11,11-tetramethyl-6-oxo-5-[(triethylsilyl)oxy]bicyclo[5.3.1]undeca-4,7-dien-2-yl benzoate C41H64O10Si2 详情 详情
(VI) 54794 (4S,5R)-3-(tert-butoxycarbonyl)-4-isobutyl-2-phenyl-1,3-oxazolidine-5-carboxylic acid C19H27NO5 详情 详情
Extended Information