(1R,3S)-1-oxothiolane-3-thiol | 127941-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (1R,3S)-1-oxothiolane-3-thiol
• CAS: 127941-63-3
• 化学式: C₄H₈OS₂
• 分子量: 136.239
• InChiKey: MXUIEFSYPPFKIF-MHTLYPKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S)-1-oxothiolane-3-thiol 、 (5R,6S)-allyl 6-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-7-oxo-3-(propylsulfinyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 三乙胺 作用下， 以 正庚烷 、 醋酸异丙酯 为溶剂， 反应 2.0h， 以55%的产率得到(3S)-3-({(5R,6S)-6-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-7-oxo-2-[(prop-2-en-1-yloxy)carbonyl]-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
  参考文献：
  名称：

  Development of a Practical and Convergent Process for the Preparation of Sulopenem

  摘要：

  Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.

  DOI：

  10.1021/op300131e
• 作为产物：
  描述：

  (S)-3-(Acetylthio)thiolane 1(R)-oxide 在 sodium ethanolate 作用下， 以 乙醇 、 醋酸异丙酯 为溶剂， 反应 0.5h， 生成 (1R,3S)-1-oxothiolane-3-thiol
  参考文献：
  名称：

  Development of a Practical and Convergent Process for the Preparation of Sulopenem

  摘要：

  Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.

  DOI：

  10.1021/op300131e

文献信息

• Development of a Practical and Convergent Process for the Preparation of Sulopenem
  作者：Steven J. Brenek、Stéphane Caron、Esmort Chisowa、Mark P. Delude、Michele T. Drexler、Marcus D. Ewing、Robert E. Handfield、Nathan D. Ide、Durgesh V. Nadkarni、Jade D. Nelson、Mark Olivier、Hahdi H. Perfect、James E. Phillips、John J. Teixeira、R. Matt Weekly、John P. Zelina

  DOI：10.1021/op300131e

  日期：2012.8.17

  Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.