(3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one | 154306-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one
• 英文别名: (3R,4S)-3-hydroxy-4-phenyl-1-[(S)-1-phenyl]ethyl-2-azetidinone；(3R,4S)-3-hydroxy-4-phenyl-1-[1-(S)-phenyl]ethyl-2-azetidinone；(3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS: 154306-81-7
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: ZQYVUTPAPKYYNK-VBNZEHGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 4-甲基苯磺酸吡啶 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 20.0~80.0 ℃ 、2.38 MPa 条件下， 反应 80.5h， 生成 (4S,5R)-2,2-二甲基-4-苯基-3-叔丁氧基羰基-3,5-氧氮杂环戊烷甲酸
  参考文献：
  名称：

  A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs

  摘要：

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).

  DOI：

  10.1016/s0040-4039(00)61724-0
• 作为产物：
  描述：

  (3R,4S)-3-methoxy-1-[(S)-α-methylbenzyl]-4-phenylazetidin-2-one 在 三溴化硼 作用下， 生成 (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one
  参考文献：
  名称：

  实用合成紫杉醇侧链。

  摘要：

  N-[（S）-甲基苄基]苯甲亚胺的手性亚胺与（Z）-α-的偶合偶合已经实现了紫杉醇侧链的N-苯甲酰基-（2R，3S）-苯基异丝氨酸甲酯的大规模合成。甲氧基三甲基甲硅烷基乙烯酮缩醛，然后依次进行内酰胺化，脱甲基，甲醇分解和N-苯甲酰化反应。

  DOI：

  10.1016/s0960-894x(98)00271-6

文献信息

• Process for the preparation of .beta.-phenylisoserine and its analogues
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05608102A1

  公开（公告）日：1997-03-04

  This invention relates to a method for preparing .beta.-phenylisoserine and analogues thereof having general formula (I) ##STR1## from an aromatic aldehyde and an .alpha.-methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of general formula (I) (R.dbd.H) may be used to prepare taxane derivatives having remarkable antitumoral and antileukaemic activity.

  这项发明涉及一种制备β-苯基异丝氨酸及其类似物的方法，其通式为(I)。从芳香醛和α-甲基芳基胺-S，以及本文所述的通式(II)的内酰胺中制备。通式(I)中的酸(R=H)可用于制备具有显著抗肿瘤和抗白血病活性的紫杉醇衍生物。
• Method for the preparation of .beta.-phenylisoserine derivatives
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05681970A1

  公开（公告）日：1997-10-28

  Method for the preparation of .beta.-phenylisoserine derivatives of general formula (I) involving the action of an anhydride and hydrogen with a product of general formula (II). The products of general formula (I) are especially useful in the preparation of taxoids having outstanding antitumour properties. In general formulae (I) and (II), Ar is an aryl radical, Ph is a phenyl radical or an optionally substituted .alpha. or .beta.-naphtyl, R is a hydrogen atom or an alkyl radical optionally substituted by a phenyl radical and R.sub.1 is an optionally substituted phenyl radical or a R.sub.2 --O radical wherein R.sub.2 is an alkyl, alkenyl, cycloalkyl, phenyl or heterocyclyl. ##STR1##

  一种制备β-苯基异丝氨酸衍生物的方法，包括使用酸酐和氢与通式（II）的产物作用。通式（I）的产物在制备具有出色抗肿瘤性能的紫杉醇中特别有用。在通式（I）和（II）中，Ar是芳基基团，Ph是苯基基团或可选择取代的α或β-萘基基团，R是氢原子或可选择取代苯基的烷基基团，R1是可选择取代的苯基基团或R2-O基团，其中R2是烷基，烯基，环烷基，苯基或杂环基。
• US5608102A
  申请人：——

  公开号：US5608102A

  公开（公告）日：1997-03-04
• A practical access to chiral phenylisoserinates, preparation of Taxotere® analogs
  作者：Jean Dominique Bourzat、Alain Commerçon

  DOI：10.1016/s0040-4039(00)61724-0

  日期：1993.9

  A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using alpha-methyl-benzylamine as the chiral template of a Staudinger reaction. Optically pure diastereoisomers 6a-c were easily recovered by crystallization. After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium. Phenylisoserinates 8b,c were used to prepare analogs of Taxotere(R).
• Practical synthesis of Taxol side chain
  作者：Hyun-Joon Ha、Gha-Seung Park、Young-Gil Ahn、Gwan Sun Lee

  DOI：10.1016/s0960-894x(98)00271-6

  日期：1998.7

  Practical large scale synthesis of N-benzoyl-(2R,3S)-phenylisoserine methyl ester of the Taxol side chain has been attained from the coupling of chiral imine of N-[(S)-methylbenzyl]benzaldimine with (Z)-alpha-methoxy trimethylsilyl ketene acetal followed by the sequential reactions of lactamization, demethylation, methanolysis and N-benzoylation.

  N-[（S）-甲基苄基]苯甲亚胺的手性亚胺与（Z）-α-的偶合偶合已经实现了紫杉醇侧链的N-苯甲酰基-（2R，3S）-苯基异丝氨酸甲酯的大规模合成。甲氧基三甲基甲硅烷基乙烯酮缩醛，然后依次进行内酰胺化，脱甲基，甲醇分解和N-苯甲酰化反应。