(2S,3S,βR)-3-<(tert-butyldimethylsilyl)oxy>-3-<(methoxycarbonyl)propyl>oxiranemethanol | 159787-29-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,βR)-3-<(tert-butyldimethylsilyl)oxy>-3-<(methoxycarbonyl)propyl>oxiranemethanol
• 英文别名: methyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3S)-3-(hydroxymethyl)oxiran-2-yl]butanoate
• CAS: 159787-29-8
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: FDNPHEDOMJESIZ-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  68.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,βR)-3-<(tert-butyldimethylsilyl)oxy>-3-<(methoxycarbonyl)propyl>oxiranemethanol 在 4-二甲氨基吡啶 、 碲化氢 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,5S)-(+)-methyl 3-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-6-heptenoate
  参考文献：
  名称：

  Synthesis of Intermediates for the Lactone Moiety of Mevinic Acids via Tellurium Chemistry

  摘要：

  Treatment of p-toluenesulfonates of epoxides of specific primary allylic alcohols with telluride ion, prepared in situ by reduction of relatively nontoxic elemental tellurium, installs the two key secondary alcohol functions that occur in the lactone part of the cholesterol-lowering drugs, compactin, mevinolin, and lovastatin. Since the epoxides of the primary allylic alcohol starting materials can be synthesized in optically active form by the Sharpless-Katsuki asymmetric epoxidation (SAE) process, the stereospecific telluride transposition can give optically active secondary allylic alcohols configured for maximum inhibition of cholesterol function.

  DOI：

  10.1021/jo00096a017
• 作为产物：
  描述：

  (3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate 在 L-(+)-酒石酸二异丙酯 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 2.0h， 生成 (2S,3S,βR)-3-<(tert-butyldimethylsilyl)oxy>-3-<(methoxycarbonyl)propyl>oxiranemethanol
  参考文献：
  名称：

  Synthesis of Intermediates for the Lactone Moiety of Mevinic Acids via Tellurium Chemistry

  摘要：

  Treatment of p-toluenesulfonates of epoxides of specific primary allylic alcohols with telluride ion, prepared in situ by reduction of relatively nontoxic elemental tellurium, installs the two key secondary alcohol functions that occur in the lactone part of the cholesterol-lowering drugs, compactin, mevinolin, and lovastatin. Since the epoxides of the primary allylic alcohol starting materials can be synthesized in optically active form by the Sharpless-Katsuki asymmetric epoxidation (SAE) process, the stereospecific telluride transposition can give optically active secondary allylic alcohols configured for maximum inhibition of cholesterol function.

  DOI：

  10.1021/jo00096a017

文献信息

• Kumar Archana, Dittmer Donald C., J. Org. Chem, 59 (1994) N 17, S 4760-4764
  作者：Kumar Archana, Dittmer Donald C.

  DOI：——

  日期：——