benzyl (E)-3-[(2R,3S)-1-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-bis(propylsulfanyl)ethyl]-3-methoxy-4-oxoazetidin-2-yl]prop-2-enoate | 162490-36-0

• 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: benzyl (E)-3-[(2R,3S)-1-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-bis(propylsulfanyl)ethyl]-3-methoxy-4-oxoazetidin-2-yl]prop-2-enoate
• CAS: 162490-36-0
• 化学式: C₃₂H₄₇NO₈S₂
• 分子量: 637.859
• InChiKey: DUVGGPWHIHKZDG-VPIULGMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (E)-3-[(2R,3S)-1-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-bis(propylsulfanyl)ethyl]-3-methoxy-4-oxoazetidin-2-yl]prop-2-enoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  The use of radical decarboxylation in the preparation of 1-methylcarbapenem antibiotic precursors from D-glucosamine

  摘要：

  The stereocontrolled synthesis of optically active 1-methylcarbapenams has been performed by radical cyclization and radical decarboxylation. 1,3,4-Trisubstituted-2-azetidinones, prepared by the Staudinger reaction with D-glucosamine as chiral auxiliary and sorbic acid were used as starting materials.

  DOI：

  10.1016/s0957-4166(00)86289-8
• 作为产物：
  描述：

  sorbic acid benzyl ester 在 二甲基硫 、 臭氧 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 benzyl (E)-3-[(2R,3S)-1-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-bis(propylsulfanyl)ethyl]-3-methoxy-4-oxoazetidin-2-yl]prop-2-enoate
  参考文献：
  名称：

  The use of radical decarboxylation in the preparation of 1-methylcarbapenem antibiotic precursors from D-glucosamine

  摘要：

  The stereocontrolled synthesis of optically active 1-methylcarbapenams has been performed by radical cyclization and radical decarboxylation. 1,3,4-Trisubstituted-2-azetidinones, prepared by the Staudinger reaction with D-glucosamine as chiral auxiliary and sorbic acid were used as starting materials.

  DOI：

  10.1016/s0957-4166(00)86289-8

文献信息

• A Regio and Stereospecific Synthesis of Carbacephem Antibiotics
  作者：Gema Ruano、Josefa Anaya、Manuel Grande

  DOI：10.1055/s-1999-3167

  日期：1999.9

  In this article we report a short and practical route to chiral carbacephems 1 based on an asymmetric Staudinger reaction for building the β-lactam ring, and on a tandem elimination-conjugate addition for making the second ring.

  在这篇文章中，我们报告了一条简短而实用的手性碳杂环化合物 1 的制备路线，该路线基于不对称施陶丁格反应来构建δ-内酰胺环，并基于串联消除-共轭加成反应来制备第二个环。