(3R,4S)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone -Drug Synthesis Database

【结构式】

【分子编号】32014

【品名】(3R,4S)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone

【CA登记号】

【分子式】C₂₀H₂₁NO₄

【分子量】339.39108

【元素组成】C 70.78% H 6.24% N 4.13% O 18.86%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IX)

4) The selective protection of baccatin III (I) with 2,2,2-trichloroethoxycarbonyl chloride and Li-HMDS in DMF gives 7-O-(2,2,2-trichloroethoxycarbonyl)baccatin III (II), which is condensed with the chiral azetidinone (IX) by means of lithium tert-butoxide or Li-HMDS in THF and the reaction product, without isolation, is treated with trifluoroacetic acid and acetic acid to afford the protected taxol derivative (X). Finally, this compound is deprotected with Zn and acetic acid.

参考文献中间体

合成目标

【1】 Gibson, F.S. (Bristol-Myers Squibb Co.); Synthesis of paclitaxel baccatin III by protecting the 7-hydroxyl using a strong base and an electrophile. WO 9945001 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	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
(II)	10448	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	C₃₄H₃₉Cl₃O₁₃	详情	详情
(IX)	32014	(3R,4S)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone	C₂₀H₂₁NO₄	详情	详情
(X)	32015	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en	C₅₀H₅₂Cl₃NO₁₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IX)

6) The selective protection of baccatin III (I) with tert-butoxycarbonyl anhydride and Li-HMDS in DMF gives 7-O-(tert-butoxycarbonyl)baccatin III (VII), which is condensed with the chiral azetidinone (IX) by means of lithium tert-butoxide or Li-HMDS in THF and the reaction product, without isolation, is treated with trifluoroacetic acid and acetic acid.

参考文献中间体

合成目标

【1】 Gibson, F.S. (Bristol-Myers Squibb Co.); Synthesis of paclitaxel baccatin III by protecting the 7-hydroxyl using a strong base and an electrophile. WO 9945001 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	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
(VII)	32011	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-9-[(tert-butoxycarbonyl)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	C₃₆H₄₆O₁₃	详情	详情
(IX)	32014	(3R,4S)-1-benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone	C₂₀H₂₁NO₄	详情	详情

Extended Information