(1'S,3R,4S)-1-(1'-phenylethyl)-3-acetoxy-4-phenylazetidin-2-one | 154428-10-1

• 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: (1'S,3R,4S)-1-(1'-phenylethyl)-3-acetoxy-4-phenylazetidin-2-one
• 英文别名: [(3R,4S)-2-oxo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-3-yl] acetate
• CAS: 154428-10-1
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: QCUYZEUTMVWGFD-DOPJRALCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 2.0h， 生成 [(3S,4R)-2-oxo-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-3-yl] acetate 、 (1'S,3R,4S)-1-(1'-phenylethyl)-3-acetoxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  An investigation towards the diastereoselective synthesis of 3-acetoxy/methoxy/phthalimido-β-lactams using chiral imines

  摘要：

  The efficient diastereoselective synthesis of 3-acetoxy/methoxy/phthalimido-beta-lactams 2/2', 3/3' and 4/4' respectively was performed using chiral imines 1 obtained from chiral amines. Factors (solvent, temperature, substituent, steric bulk) influencing the stereoselectivity and the diastereomeric ratio were also studied in detail. The diastereoselectivity of the two isomers was determined from the ratio of integral values of doublets of C3-H and C4-H and from the integral values of H in -CH(Me/Et)Ph/Np of the two diastereomers. Representative pairs of cis-diastereomers were separated by efficient column chromatography. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.007

文献信息

• 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).