(R)-4-Benzyloxymethoxy-3-hydroxymethyl-butyric acid tert-butyl ester | 201804-37-7

• 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: (R)-4-Benzyloxymethoxy-3-hydroxymethyl-butyric acid tert-butyl ester
• 英文别名: tert-butyl (3R)-3-(hydroxymethyl)-4-(phenylmethoxymethoxy)butanoate
• CAS: 201804-37-7
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: RQEJCNNZJIQDAU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  (R)-4-Benzyloxymethoxy-3-hydroxymethyl-butyric acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以70%的产率得到(+)-3-(benzyloxymethoxymethyl)-4-butanolide
  参考文献：
  名称：

  Chemoenzymatic synthesis of asymmetrized bis(hydroxymethyl)propanoates (BHYMP∗) as a new family of chiral building blocks

  摘要：

  A series of asymmetrized bis(hydroxymethyl)propanoates (BHYMP*) has been prepared in both enantiomeric forms through a chemoenzymatic methodology involving complementary diacetate monohydrolyses and diol monoacetylations catalyzed by lipases. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00560-0
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 sodium hydroxide 、 Wilkinson's catalyst 、 buffer (K₂HPO₄-KH₂PO₄) pH 7 、 lipase Amano AY 、 phosphate buffer pH=7 、 pig panereatic lipase 、 水 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 异丙醚 、 苯 为溶剂， -30.0~40.0 ℃ 、506.62 kPa 条件下， 反应 63.33h， 生成 (R)-4-Benzyloxymethoxy-3-hydroxymethyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of asymmetrized bis(hydroxymethyl)propanoates (BHYMP∗) as a new family of chiral building blocks

  摘要：

  A series of asymmetrized bis(hydroxymethyl)propanoates (BHYMP*) has been prepared in both enantiomeric forms through a chemoenzymatic methodology involving complementary diacetate monohydrolyses and diol monoacetylations catalyzed by lipases. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00560-0

文献信息

• Protecting group controlled stereoselective alkylation of asymmetrized bis(hydroxymethyl)propanoates (BHYMP*)
  作者：Luca Banfi、Giuseppe Guanti

  DOI：10.1016/s0957-4166(99)00006-3

  日期：1999.2

  The diastereoselective methylation of the enolates derived from some asymmetrized bis(hydroxymethyl)propanoates (BHYMP*) has been studied. Good results were achieved when one of the two hydroxymethyl groups was unprotected. The induction was interpreted on the basis of an acyclic stereocontrol governed by stereoelectronic effects. (C) 1999 Elsevier Science Ltd. All rights reserved.