methyl (2S,3S)-2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-3-phenypropanonate | 1088697-92-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2S,3S)-2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-3-phenypropanonate
• CAS: 1088697-92-0
• 化学式: C₂₆H₃₀O₄Si
• 分子量: 434.607
• InChiKey: WDPDTRYFPFKAIH-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-3-phenypropanonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以91%的产率得到(2S,3S)-2,3-dihydroxy-3-phenylpropanoic acid methyl ester
  参考文献：
  名称：

  Anti and Syn Glycolate Aldol Reactions with a Readily Displaced Thiol Auxiliary

  摘要：

  GraphicsThe TBDPS protected glycolate derivative of thiol auxiliary 1 is readily prepared (3 steps, 80% overall yield) and has been shown to give excellent anti:syn selectivity (>97.3) and high facial selectivity (88:12 to 97:3) in glycolate aldol reactions with a range of aldehydes (75-87% isolated yield major diastereomer). In contrast, its benzyl protected counterpart displays more versatility with respect to the generation of either anti or syn glycolate aldol adducts, but only modest facial selectivity. The thiol auxiliary has been shown to be readily displaced under mild conditions to give alcohol and ester derivatives of the glycolate aldol adducts.

  DOI：

  10.1021/jo801720v
• 作为产物：
  描述：

  (1'S,2S,2'R,3S)-S-[2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl] 2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-3-phenylthiopropionate 、 sodium methylate 在 甲醇 作用下， 反应 0.92h， 以37%的产率得到methyl (2S,3S)-2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-3-phenypropanonate
  参考文献：
  名称：

  Anti and Syn Glycolate Aldol Reactions with a Readily Displaced Thiol Auxiliary

  摘要：

  GraphicsThe TBDPS protected glycolate derivative of thiol auxiliary 1 is readily prepared (3 steps, 80% overall yield) and has been shown to give excellent anti:syn selectivity (>97.3) and high facial selectivity (88:12 to 97:3) in glycolate aldol reactions with a range of aldehydes (75-87% isolated yield major diastereomer). In contrast, its benzyl protected counterpart displays more versatility with respect to the generation of either anti or syn glycolate aldol adducts, but only modest facial selectivity. The thiol auxiliary has been shown to be readily displaced under mild conditions to give alcohol and ester derivatives of the glycolate aldol adducts.

  DOI：

  10.1021/jo801720v