4,4'-Thiobis<(3S,4R)-3-<(1R)-1-<(dimethyl-tert-butylsilyl)oxy>ethyl>-2-azetidinone> | 142438-86-6

• 英文名称: 4,4'-Thiobis<(3S,4R)-3-<(1R)-1-<(dimethyl-tert-butylsilyl)oxy>ethyl>-2-azetidinone>
• 英文别名: 4,4'-Thiobis((3S,4R)-3-{(1R)-1-[(dimethyl-tert-butylsilyl)oxy]ethyl}-2-azetidinone)
• CAS: 142438-86-6
• 化学式: C₂₂H₄₄N₂O₄SSi₂
• 分子量: 488.839
• InChiKey: JVSWJCODFIAWQQ-OQTPBVATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone 在 sodium acetate 作用下， 以 异丙醇 为溶剂， 反应 14.0h， 以211 mg的产率得到(3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-azetidinone
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00042a010