(2R,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-3-phenylpropanoic acid methyl ester | 262844-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-3-phenylpropanoic acid methyl ester
• 英文别名: methyl (2R,3S)-2-O-t-butyldimethylsilyl-2,3-dihydroxy-3-phenylpropionate；methyl (2R,3S)-2-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-3-phenylpropanoate
• CAS: 262844-04-2
• 化学式: C₁₆H₂₆O₄Si
• 分子量: 310.466
• InChiKey: RAKTWTREMCNAAY-UONOGXRCSA-N

物化性质

• 沸点：
  373.2±42.0 °C(predicted)
• 密度：
  1.039±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-3-phenylpropanoic acid methyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 甲基 (2R,3S)-(+)-2,3-二羟基-3-苯基丙酸盐
  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：

  methyl (2R,3S)-2-O-t-butyldimethylsilyl-3-O-formyl-2,3-dihydroxy-3-phenylpropionate 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到(2R,3S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-3-phenylpropanoic 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

文献信息

• Lewis Base Activation of Lewis Acids: Catalytic, Enantioselective Addition of Glycolate-Derived Silyl Ketene Acetals to Aldehydes
  作者：Scott E. Denmark、Won-jin Chung

  DOI：10.1021/jo8006539

  日期：2008.6.1

  A catalytic system involving silicon tetrachloride and a chiral, Lewis basic bisphosphoramide catalyst is effective for the addition of glycolate-derived silyl ketene acetals to aldehydes. It was found that the sense of diastereoselectivity could be modulated by changing the size of the substituents on the silyl ketene acetals. In general, the trimethylsilyl ketene acetals derived from methyl glycolates

  涉及四氯化硅和手性路易斯碱性双磷酰胺催化剂的催化体系可有效地将乙醇酸衍生的甲硅烷基烯酮缩醛添加到醛中。发现可以通过改变甲硅烷基烯酮缩醛上取代基的大小来调节非对映选择性。一般情况下，三甲基甲硅烷烯酮缩醛选自甲基甘醇酸酯衍生的与α-氧气的大型保护基提供对映体富集的α，β二羟基酯具有高顺式-diastereoselectivity，而叔丁基二烯酮缩醛从α-笨重的酯衍生的甲氧基乙酸提供对映体富集的α，高β二羟基酯抗-diastereoselecitvity。