(2R,3S,4S)-methyl 5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethylpentanoate | 1137584-19-0

• 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: (2R,3S,4S)-methyl 5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethylpentanoate
• 英文别名: methyl (2R,3S,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4-dimethylpentanoate
• CAS: 1137584-19-0
• 化学式: C₁₄H₃₀O₄Si
• 分子量: 290.475
• InChiKey: DYTCDFJOIQFQDY-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-methyl 5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethylpentanoate 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(2R,3S,4S)-methyl 3,5-bis(tert-butyldimethylsilyloxy)-2,4-dimethylpentanoate
  参考文献：
  名称：

  Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates

  摘要：

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.

  DOI：

  10.1021/ol802850w
• 作为产物：
  描述：

  、 (2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以60%的产率得到(2R,3S,4S)-methyl 5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethylpentanoate
  参考文献：
  名称：

  Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates

  摘要：

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.

  DOI：

  10.1021/ol802850w

文献信息

• Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates
  作者：P. Veeraraghavan Ramachandran、Debarshi Pratihar

  DOI：10.1021/ol802850w

  日期：2009.4.2

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.