3S,4R-4-[t-Butylthio(thiocarbonyl)thio]-3-[1R-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone | 112206-96-9

• 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: 3S,4R-4-[t-Butylthio(thiocarbonyl)thio]-3-[1R-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone
• 英文别名: 3S,4R-4-[t-Butylthio(thiocarbonyl)thio]-3[1R-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone；(3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-tert-butylsulfanylcarbothioylsulfanylazetidin-2-one
• CAS: 112206-96-9
• 化学式: C₁₆H₃₁NO₂S₃Si
• 分子量: 393.711
• InChiKey: RFWITBGSHMDSFO-NTZNESFSSA-N

物化性质

• 沸点：
  508.0±43.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  trithiocarbonic acid mono-tert-butyl ester 、 4-乙酰氧基氮杂环丁酮 以 甲基叔丁基醚 、 mineral oil 为溶剂， 反应 1.0h， 生成 3S,4R-4-[t-Butylthio(thiocarbonyl)thio]-3-[1R-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone
  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

• Process for penem derivatives
  申请人：Pfizer Inc.

  公开号：US04782145A1

  公开（公告）日：1988-11-01

  An efficient process for converting readily available 4-acetoxy-2-azetidinones to allyl 2-thioxopenam-3-carboxylates, intermediates useful for the synthesis of penem antibiotics.

  一种高效的过程，将易得的4-乙酰氧基-2-氮杂环戊酮转化为烯丙基2-硫代戊内酰胺-3-羧酸酯，这是合成青霉烷类抗生素的有用中间体。
• 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.