(2S,4R,5S)-4-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-phenylpentan-3-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4R,5S)-4-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-phenylpentan-3-one
• 英文别名: (2R,3S)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-3-phenylpropan-1-one
• 化学式: C₃₀H₃₆O₅Si
• 分子量: 504.698
• InChiKey: BDBQDNBZVJQISK-UNCTUWKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 、 1-O-t-butyldiphenylsilyl-3,4-O-isopropylidene-L-erythrulose 在 氯代二环己基硼烷 、 三乙胺 、 双氧水 作用下， 以 乙醚 、 甲醇 、 phosphate buffer 为溶剂， 反应 7.0h， 以78%的产率得到(2S,4R,5S)-4-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-phenylpentan-3-one
  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.