N-[(1S,2R)-3-[(1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]dec-4-yl]-2-[(4-methoxybenzyl)oxy]-3-oxo-1-phenylpropyl]benzamide -Drug Synthesis Database

【结构式】

【分子编号】10613

【品名】N-[(1S,2R)-3-[(1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]dec-4-yl]-2-[(4-methoxybenzyl)oxy]-3-oxo-1-phenylpropyl]benzamide

【CA登记号】

【分子式】C₃₄H₃₈N₂O₆S

【分子量】602.7516

【元素组成】C 67.75% H 6.35% N 4.65% O 15.93% S 5.32%

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：(V)

A new synthesis of paclitaxel has been described: The condensation of Oppolzer's L-(+)-2,10-camphorsultam (I) with 2-(4-methoxybenzyloxy)acetyl chloride (II) by means of NaH gives the corresponding substituted sultam (III), which is condensed with N-benzoylbenzaldehydeimine (IV) by means of lithium bis(trimethylsilyl)amide, yielding the protected side-chain (V) of paclitaxel. The reaction of (V) with DDQ affords oxazolidine (VI), which is hydrolyzed with LiOH/H2O2 to the free oxazolidine-carboxylic acid (VII). The esterification of (VII) with baccatin III (VIII) by means of dicyclohexylcarbodiimide (DCC) affords the protected paclitaxel derivative (IX), which is finally treated with HCl in ethanol.

参考文献中间体

合成目标

【1】 Kanazawa, A.M.; Greene, A.E.; Denis, J.-N.; Direct, stereoselective synthesis of the protected paclitaxel (Taxol) side chain and high-yield transformation to paclitaxel. J Chem Soc Chem Commun 1994, 2591.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	10609	(1R,5S,7S)-10,10-Dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione	C₁₀H₁₇NO₂S	详情	详情
(II)	10610	2-[(4-Methoxybenzyl)oxy]acetyl chloride	C₁₀H₁₁ClO₃	详情	详情
(III)	10611	(1R,5S,7S)-4-[2-[(4-Methoxybenzyl)oxy]acetyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione	C₂₀H₂₇NO₅S	详情	详情
(IV)	10612	N-[(Z)-Benzylidene]benzamide	C₁₄H₁₁NO	详情	详情
(V)	10613	N-[(1S,2R)-3-[(1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]dec-4-yl]-2-[(4-methoxybenzyl)oxy]-3-oxo-1-phenylpropyl]benzamide	C₃₄H₃₈N₂O₆S	详情	详情
(VI)	10614	(1R,5S,7S)-4-[[(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidin-5-yl]carbonyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione	C₃₄H₃₆N₂O₆S	详情	详情
(VII)	10615	(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid	C₂₄H₂₁NO₅	详情	详情
(VIII)	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
(IX)	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

Extended Information