(2S,3R)-2-Bromo-3-hydroxy-2-methyl-5-phenyl-pentanoic acid ethyl ester | 285565-02-8

• 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: (2S,3R)-2-Bromo-3-hydroxy-2-methyl-5-phenyl-pentanoic acid ethyl ester
• 英文别名: ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-5-phenylpentanoate
• CAS: 285565-02-8
• 化学式: C₁₄H₁₉BrO₃
• 分子量: 315.207
• InChiKey: UHRQXSVDDNVPEA-OCCSQVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-Bromo-3-hydroxy-2-methyl-5-phenyl-pentanoic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到(2R,3R)-2-Methyl-3-phenethyl-oxirane-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Efficient enantio- and diastereoselective synthesis of enantiopure syn-α-bromo-β-hydroxy-α-methylpropionate esters and their cis-α,β-epoxy derivatives based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction

  摘要：

  syn-alpha-Bromo-beta-hydroxy-alpha-methylpropionate esters were prepared in high diastereoselectivity with essentially enantiopure state by employing the chiral oxazaborolidinone-promoted asymmetric aldol reaction with beta-bromo-beta-methylketene silyl acetal. The subsequent subjection of the alpha-bromo-beta-hydroxy esters to basic conditions led to the quantitative transformation to the corresponding enantiopure cis-alpha,beta-epoxy derivatives, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00089-6
• 作为产物：
  描述：

  苯丙醛 、 2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene 在 N-(p-toluenesulfonyl)-L-valine 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2S,3R)-2-Bromo-3-hydroxy-2-methyl-5-phenyl-pentanoic acid ethyl ester 、 (2S,3S)-2-Bromo-3-hydroxy-2-methyl-5-phenyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  Efficient enantio- and diastereoselective synthesis of enantiopure syn-α-bromo-β-hydroxy-α-methylpropionate esters and their cis-α,β-epoxy derivatives based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction

  摘要：

  syn-alpha-Bromo-beta-hydroxy-alpha-methylpropionate esters were prepared in high diastereoselectivity with essentially enantiopure state by employing the chiral oxazaborolidinone-promoted asymmetric aldol reaction with beta-bromo-beta-methylketene silyl acetal. The subsequent subjection of the alpha-bromo-beta-hydroxy esters to basic conditions led to the quantitative transformation to the corresponding enantiopure cis-alpha,beta-epoxy derivatives, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00089-6

文献信息

• A Divergent Synthesis of Essentially Enantiopure<i>syn</i>- and<i>anti</i>-Propionate Aldol Adducts Based on the Chiral 1,3,2-Oxazaborolidin-5-one-Promoted Asymmetric Aldol Reaction Followed by Diastereoselective Radical Reduction
  作者：Syun-ichi Kiyooka、Kazi Abuds Shahid

  DOI：10.1246/bcsj.74.1485

  日期：2001.8

  Essentially, enantiopure syn- and anti-propionate aldol adducts were divergently synthesized using a novel strategy which utilizes both the highly enantioselective 1,3,2-oxazaborolidin-5-one-promoted aldol reaction with a ketene silyl acetal derived from ethyl 2-bromo propionate and a highly diastereoselective radical debromination reaction. These procedures provide yields that increase to a level

  本质上，对映纯的合成和反丙醇醛加合物是使用一种新的策略不同地合成的，该策略利用高度对映选择性的 1,3,2-oxazaborolidin-5-one-促进的醛醇反应与衍生自乙基 2-溴的乙烯酮甲硅烷基缩醛丙酸盐和高度非对映选择性的自由基脱溴反应。这些程序提供的产率增加到可用于实际合成的水平。