S-tert-butyl (2R*,3R*)-2-ethyl-3-hydroxy-3-<2-(trimethylsilyl)phenyl>propanethioate | 139348-15-5

• 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: S-tert-butyl (2R*,3R*)-2-ethyl-3-hydroxy-3-<2-(trimethylsilyl)phenyl>propanethioate
• 英文别名: S-tert-butyl (2R*,3R*)-2-ethyl-3-hydroxy-3-[2-(trimethylsilyl)phenyl]propanethioate；S-tert-butyl (2R)-2-[(R)-hydroxy-(2-trimethylsilylphenyl)methyl]butanethioate
• CAS: 139348-15-5；139348-16-6；139405-82-6；139405-83-7；139405-84-8；139405-85-9
• 化学式: C₁₈H₃₀O₂SSi
• 分子量: 338.587
• InChiKey: MZHKQWRWAIAQKI-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1(tert-Butylthio)-1-(trimethylsilyloxy)but-1-ene 在 ammonium cerium(IV) nitrate 、 (Sp)-tricarbonyl[η6-2-(trimethylsilyl)benzaldehyde]chromium(0) 、 四氯化钛 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 S-tert-butyl (2R*,3S*)-2-ethyl-3-hydroxy-3-<2-(trimethylsilyl)phenyl>propanethioate 、 S-tert-butyl (2R*,3R*)-2-ethyl-3-hydroxy-3-<2-(trimethylsilyl)phenyl>propanethioate
  参考文献：
  名称：

  Optically active tricarbonyl[.eta.6-o-(trimethylsilyl)benzaldehyde]chromium(0) complexes in organic synthesis: a highly anti-selective asymmetric aldol reaction with O-silyl ketene O,S-acetals

  摘要：

  Treatment of optically pure (+)-tricarbonyl[o-(trimethylsilyl)benzaldehyde]chromium(0), (+)-1, with O-silyl ketene O,S-acetals 4c-f afforded, after decomplexation, the (-)-anti-aldol products (-)-5c-f, while an antipode, (-)-1, provided the (+)-anti ones (+)-5c-f. Optical purity of these aldol products were determined to be in a range of 92 to > 98% ee. The absolute configuration was established by an X-ray crystallographic analysis.

  DOI：

  10.1021/jo00033a025

文献信息

• Optically active tricarbonyl[.eta.6-o-(trimethylsilyl)benzaldehyde]chromium(0) complexes in organic synthesis: a highly anti-selective asymmetric aldol reaction with O-silyl ketene O,S-acetals
  作者：Chisato Mukai、Motonori Miyakawa、Ado Mihira、Miyoji Hanaoka

  DOI：10.1021/jo00033a025

  日期：1992.3

  Treatment of optically pure (+)-tricarbonyl[o-(trimethylsilyl)benzaldehyde]chromium(0), (+)-1, with O-silyl ketene O,S-acetals 4c-f afforded, after decomplexation, the (-)-anti-aldol products (-)-5c-f, while an antipode, (-)-1, provided the (+)-anti ones (+)-5c-f. Optical purity of these aldol products were determined to be in a range of 92 to > 98% ee. The absolute configuration was established by an X-ray crystallographic analysis.