2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid tert-butyl ester | 111596-53-3

• 英文名称: 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid tert-butyl ester
• 英文别名: S-tert-butyl 2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanethioate
• CAS: 111596-53-3；111687-82-2
• 化学式: C₁₈H₃₅NO₃SSi
• 分子量: 373.632
• InChiKey: IIJQLXSVTXTHHR-DGKWRVCWSA-N

物化性质

• 沸点：
  448.0±10.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid tert-butyl ester 、 sodium hydroxide 生成 2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanoic acid
  参考文献：
  名称：

  ENDO, MASAKI, CAN. J. CHEM., 65,(1987) N 9, 2140-2245

  摘要：

  DOI：
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 21.0h， 生成 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl}thiopropionic acid tert-butyl ester
  参考文献：
  名称：

  1β-Methylcarbapenem intermediates via the thiolysis of a Meldrum's precursor

  摘要：

  5-{3-[1-(tert-Butyidimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-2,2,5-trimethyl-[1,3]dioxane-4,6-dione (3) has been submitted to nucleophilic attack with various nucleophiles. Meldrum's moiety transesterification, C4-substitution, beta -lactam ring opening and Meldrum's moiety decarboxylation were observed. Reaction of 3 with ethanethiol and dimethylaminopyridine in ethanol quantitatively furnished ethyl 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-thiopropionate as the 1:1 mixture of beta (7a) and alpha (8a) diastereoisomers. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01082-1

文献信息

• Syntheses of chiral intermediates of 1-β-methylcarbapenems: (3<i>S</i>,4<i>R</i>)-3-[1(<i>R</i>)-<i>tert</i>-butyldimethylsilyloxyethyl]-4-chloroazetidin-2-one and (3<i>S</i>,4<i>S</i>)-3-[1(<i>R</i>)-<i>tert</i>-butyldimethylsilyloxyethyl]-4-[1(<i>R</i>)-<i>tert</i>-butylthiocarbonylethyl]azetidin-2-one
  作者：Masaki Endo

  DOI：10.1139/v87-357

  日期：1987.9.1

  The 4-chloroazetidinone 10, a very reactive chiral intermediate for 1-β-methylcarbapenems (1b), was easily prepared and isolated as a solid crystalline compound from the corresponding sulfide 5. Another chiral intermediate (16d) bearing the 1-β-methyl moiety was prepared by stereoselective aldol type condensation of either azetidinone 4 or 10 with metal enolates 14 (R = S—Bu′, M = ZrCp₂Cl, [Formula: see text], and SnBr). The β/α ratios were 9:1, 3:1, 2:1 respectively.

  4-氯吡嗪酮10是1-β-甲基卡巴比林（1b）的非常活性手性中间体，可以从相应的硫醚5中轻松制备并分离为固体结晶化合物。另一个携带1-β-甲基基团的手性中间体（16d）是通过对吡嗪酮4或10与金属烯醇酸盐14（R = S—Bu'，M = ZrCp2Cl，[Formula: see text]和SnBr）的立体选择性醛缩反应制备的。β/α比例分别为9:1，3:1，2:1。