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【结 构 式】

【分子编号】10741

【品名】ethyl (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-3-phenylpropanoate

【CA登记号】

【 分 子 式 】C19H21NO5

【 分 子 量 】343.37948

【元素组成】C 66.46% H 6.16% N 4.08% O 23.3%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

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).

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
Extended Information