(3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-(isopropoxy)-2-azetidinone | 142407-60-1

• 英文名称: (3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-(isopropoxy)-2-azetidinone
• 英文别名: (3R,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-isopropoxyazetidin-2-one；(3R,4R)-3-((1R)-1-tert-butyldimethylsilyloxyethyl)-4-isopropoxyazetidin-2-one；(3R,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-propan-2-yloxyazetidin-2-one
• CAS: 142407-60-1
• 化学式: C₁₄H₂₉NO₃Si
• 分子量: 287.475
• InChiKey: ZNOQELVQEHJNDS-NTZNESFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S,4R)-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-4-phenylthioazetidin-2-one 在 三氟甲磺酸三甲基硅酯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 16.33h， 生成 (3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-(isopropoxy)-2-azetidinone
  参考文献：
  名称：

  A Novel Method for the Alkoxylation of Azetidin-2-ones at the 4-Position.

  摘要：

  在一定量的三甲基硅基三氟甲磺酸盐催化下，4-亚磺酰基氮杂环丁烷-2-酮与各种类型的三丁基锡烷氧基化合物发生反应，以高产率得到相应的反式烷氧基氮杂环丁烷-2-酮。

  DOI：

  10.1248/cpb.40.1044

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.