(1'S,2S,2'R,3S)-S-[2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl] 2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-4-methyl-thiopentanoate | 1088697-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1'S,2S,2'R,3S)-S-[2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl] 2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-4-methyl-thiopentanoate
• 英文别名: S-[(1S,2R)-2-[benzyl-(2,4,6-trimethylphenyl)sulfonylamino]-1-phenylpropyl] (2S,3S)-2-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-4-methylpentanethioate
• CAS: 1088697-53-3
• 化学式: C₄₇H₅₇NO₅S₂Si
• 分子量: 808.191
• InChiKey: KGXYZAMIUQIJPZ-MHNLDWOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1'S,2'R)-S-[2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl] 2-(tert-butyl(diphenyl)silyloxy)-thioacetate 、 异丁醛 在 三乙胺 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 以77%的产率得到(1'S,2S,2'R,3S)-S-[2'-(N-benzyl-N-mesitylenesulfonylamino)-1'-phenylpropyl] 2-(tert-butyl(diphenyl)silyloxy)-3-hydroxy-4-methyl-thiopentanoate
  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

文献信息

• <i>Anti</i> and <i>Syn</i> Glycolate Aldol Reactions with a Readily Displaced Thiol Auxiliary
  作者：Sandra Fanjul、Alison N. Hulme

  DOI：10.1021/jo801720v

  日期：2008.12.19

  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.