methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-4-methylpentanoate | 262843-99-2

• 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: methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-4-methylpentanoate
• 英文别名: methyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-formyloxy-4-methylpentanoate
• CAS: 262843-99-2
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: WFAVLZTZOUCIRS-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-4-methylpentanoate 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以78%的产率得到(2R,3S)-2,3-dihydroxy-4-methylpentanoic acid methyl ester
  参考文献：
  名称：

  Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn -α,β-Dihydroxy Esters

  摘要：

  Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2-syn/1,3-syn stereoisomer. Through oxidative cleavage of the aldol adducts with periodic acid hydrate, enantiopure syn-alpha,beta-dihydroxy esters with either hydroxyl group differently protected have been prepared. These erythrulose derivatives therefore behave as a chiral hydroxy acetate (glycolate) enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01041-8
• 作为产物：
  描述：

  重氮甲烷 、 (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-6-methylheptan-3-one 在 高碘酸 作用下， 以 乙酸乙酯 、 乙醚 为溶剂， 反应 2.0h， 以66%的产率得到methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-4-methylpentanoate
  参考文献：
  名称：

  Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn -α,β-Dihydroxy Esters

  摘要：

  Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2-syn/1,3-syn stereoisomer. Through oxidative cleavage of the aldol adducts with periodic acid hydrate, enantiopure syn-alpha,beta-dihydroxy esters with either hydroxyl group differently protected have been prepared. These erythrulose derivatives therefore behave as a chiral hydroxy acetate (glycolate) enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01041-8

文献信息

• Aldol Reactions with Erythrulose Derivatives: Stereoselective Synthesis of Differentially Protected syn -α,β-Dihydroxy Esters
  作者：M. Carda、J. Murga、E. Falomir、F. González、J.A. Marco

  DOI：10.1016/s0040-4020(99)01041-8

  日期：2000.1

  Boron enolates of 1-O-silylated erythrulose 3,4-acetonides prepared with Brown's chloro-dicyclohexylborane/tertiary amine system have been shown to react with achiral aldehydes in a highly stereoselective way to yield a 1,2-syn/1,3-syn stereoisomer. Through oxidative cleavage of the aldol adducts with periodic acid hydrate, enantiopure syn-alpha,beta-dihydroxy esters with either hydroxyl group differently protected have been prepared. These erythrulose derivatives therefore behave as a chiral hydroxy acetate (glycolate) enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.