(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 | 127997-21-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (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
• 英文别名: Allyl 5R,6S-6-[1R-1-(t-Butyldimethylsilyloxy)ethyl]-2-(cis-1-oxo-3-thiolanylthio)-2penem-3-carboxylate；Allyl 5R,6S-6-[1R-(Dimethyl-t-butylsilyloxy)ethyl]-2-[(1R-oxo-3S-thiolanyl)thio]penem-3-carboxylate；YS6Zym62F2；prop-2-enyl (5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7-oxo-3-[(1R,3S)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 127997-21-1
• 化学式: C₂₁H₃₃NO₅S₃Si
• 分子量: 503.78
• InChiKey: VBAWLPWZTCQUFD-SMZGFATLSA-N

物化性质

• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (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 在 sodium benzenesulfonate 、 palladium diacetate 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以176.02 g的产率得到(3S)-3-({(5R,6S)-6-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-2-carboxy-7-oxo-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：

  (5R,6S)-allyl 6-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-7-oxo-3-(propylthio)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 六氟异丙醇 、 过氧化脲素 、 三乙胺 作用下， 以 正庚烷 、 醋酸异丙酯 、 甲苯 为溶剂， 反应 2.0h， 生成 (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

文献信息

• 1-aza-4,5-dithiabicyclo [4.2.0] oct-2-en-8-one-2 carboxylate esters
  申请人：Pfizer Inc.

  公开号：US04695626A1

  公开（公告）日：1987-09-22

  1-aza-4,5-dithiabicyclo [4.2.0] oct-2-en-8-one-2 carboxylate ester intermediates useful for the synthesis of penems.

  1-aza-4,5-dithiabicyclo[4.2.0]oct-2-en-8-one-2羧酸酯中间体，对于合成青霉烷类药物有用。
• BRIGHTY, KATHERINE E.
  作者：BRIGHTY, KATHERINE E.

  DOI：——

  日期：——
• 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.