(3S,4S)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone | 112206-93-6

• 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,4S)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone
• 英文别名: (3S,4S)-3-{(1R)-1-[(Dimethyl-tert-butylsilyl)oxy]ethyl}-4-({[(1(R)-oxo-3(S)-thiolanyl)thio]thiocarbonyl}thio)-2-azetidinone；(3S,4S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,3S)-1-oxothiolan-3-yl]sulfanylcarbothioylsulfanylazetidin-2-one
• CAS: 112206-93-6；112295-83-7；115793-24-3；142507-63-9
• 化学式: C₁₆H₂₉NO₃S₄Si
• 分子量: 439.761
• InChiKey: DLELPBQVHWHPES-KJRCMOLDSA-N

物化性质

• 沸点：
  640.4±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone 、 allyl 2-oxoacetate 生成 prop-2-enyl (2S)-2-[(3S,4S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2-oxo-4-[(1R,3S)-1-oxothiolan-3-yl]sulfanylcarbothioylsulfanylazetidin-1-yl]-2-hydroxyacetate
  参考文献：
  名称：

  BRIGHTY, KATHERINE E.

  摘要：

  DOI：
• 作为产物：
  描述：

  1-oxo-3-(methylcarbonylthio)-thiolane 、 4-乙酰氧基氮杂环丁酮 生成 (3S,4S)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone
  参考文献：
  名称：

  BRIGHTY, KATHERINE E.

  摘要：

  DOI：

文献信息

• 2-Thioalkyl penems: an efficient synthesis of sulopenem, a (5R,6S)-6-(1(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem antibacterial
  作者：Robert A. Volkmann、Paul R. Kelbaugh、Deane M. Nason、V. John Jasys

  DOI：10.1021/jo00042a010

  日期：1992.7

  A practical synthesis of potent penem antibacterials, CP-70,429 (1) (sulopenem) and CP-81,054 (2), is described. (L)-Aspartic acid was utilized to generate both the (3S)- and (3R)-thiolanylthio side chains of (5R,6S)-6-(1-(R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl)thio]-2-penem-3-carboxylic acids 1 and 2. This synthetic pathway provided in high yield enantiopure thioacetate intermediates 15 and 19. To accommodate the fragile side chain sulfoxide moiety of the targeted beta-lactams, standard penem synthetic methodology was modified to facilitate the conversion of 15 and 19 to 1 and 2. The reactive chloroazetidinone 4b was utilized to generate key azetidinone trithiocarbonate intermediate 22 which contains the requisite penem side chain. A chemoselective oxalofluoride-based azetidinone N-acylation procedure, which avoids sulfoxide O-acylation, was required for the conversion of 22 to the penem framework.
• BRIGHTY, KATHERINE E.
  作者：BRIGHTY, KATHERINE E.

  DOI：——

  日期：——