(2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-6-methylheptan-3-one | 220820-63-3

• 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-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-6-methylheptan-3-one
• 英文别名: (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-4-methylpentan-1-one
• CAS: 220820-63-3
• 化学式: C₁₇H₃₄O₅Si
• 分子量: 346.539
• InChiKey: HMKKJNKFQODCHQ-KCQAQPDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-6-methylheptan-3-one 在 锂硼氢 、 oxonium 、 hydroxide 、 氢气 作用下， 生成
  参考文献：
  名称：

  Erythrulose as a multifunctional chiron: Highly stereoselective boron aldol additions

  摘要：

  We have investigated the formation of various metal enolates of 1-O-silylated erythrulose 3,4-acetonides. We were able to prepare boron enolates using Brown's dicyclohexylboron chloride/tertiary amine system. When these enolates were allowed to react with a range of achiral aldehydes, highly stereoselective aldol additions took place with formation of the syn/syn stereoisomer. This has been attributed to the exclusive formation of a Z boron enolate, which is in a sharp contrast with the usual behaviour of the aforementioned reagent. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)80113-0
• 作为产物：
  描述：

  2-[tert-butyl(dimethyl)silyl]oxy-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanone 、 异丁醛 在 氯代二环己基硼烷 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-6-methylheptan-3-one
  参考文献：
  名称：

  Erythrulose derivatives as functionalized chiral d3 and d4 synthons

  摘要：

  Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d(3) or d(4) synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00638-9

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.
• Erythrulose derivatives as functionalized chiral d3 and d4 synthons
  作者：Juan Murga、Eva Falomir、Miguel Carda、J.Alberto Marco

  DOI：10.1016/s0957-4166(02)00638-9

  日期：2002.10

  Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d(3) or d(4) synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Erythrulose as a multifunctional chiron: Highly stereoselective boron aldol additions
  作者：J.Alberto Marco、Miguel Carda、Eva Falomir、Claudio Palomo、Mikel Oiarbide、J.Aurelio Ortiz、Anthony Linden

  DOI：10.1016/s0040-4039(99)80113-0

  日期：1999.1

  We have investigated the formation of various metal enolates of 1-O-silylated erythrulose 3,4-acetonides. We were able to prepare boron enolates using Brown's dicyclohexylboron chloride/tertiary amine system. When these enolates were allowed to react with a range of achiral aldehydes, highly stereoselective aldol additions took place with formation of the syn/syn stereoisomer. This has been attributed to the exclusive formation of a Z boron enolate, which is in a sharp contrast with the usual behaviour of the aforementioned reagent. (C) 1999 Elsevier Science Ltd. All rights reserved.