(S)-3-Hydroxy-4,4-dimethoxy-butyric acid methyl ester | 323201-62-3

• 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: (S)-3-Hydroxy-4,4-dimethoxy-butyric acid methyl ester
• 英文别名: methyl (3S)-3-hydroxy-4,4-dimethoxybutanoate
• CAS: 323201-62-3
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: YNXPWAURQGZFPN-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (S)-3-Hydroxy-4,4-dimethoxy-butyric acid methyl ester 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (2R,3S)-2-Hydrazino-3-hydroxy-4,4-dimethoxy-butyric acid methyl ester
  参考文献：
  名称：

  Efficient asymmetric synthesis of a functionalized Δ2-pyrazoline

  摘要：

  The first asymmetric synthesis of the (4S,SR)-5-carbomethoxy-4-hydroxy-Delta (2)-pyrazoline in four steps is described starting from the methyl 4,4-dimethoxy-3-oxobutanoate by sequential catalytic hydrogenation and electrophilic amination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01582-3
• 作为产物：
  描述：

  4,4-二甲氧基乙酰乙酸甲酯 在 [(R)-Binap RuCl₂]2 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以83%的产率得到(S)-3-Hydroxy-4,4-dimethoxy-butyric acid methyl ester
  参考文献：
  名称：

  Efficient asymmetric synthesis of a functionalized Δ2-pyrazoline

  摘要：

  The first asymmetric synthesis of the (4S,SR)-5-carbomethoxy-4-hydroxy-Delta (2)-pyrazoline in four steps is described starting from the methyl 4,4-dimethoxy-3-oxobutanoate by sequential catalytic hydrogenation and electrophilic amination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01582-3

文献信息

• Diastereoselective syntheses of α-amino-β-hydroxyesters precursors of the ribosyl-diazepanone core of the liposidomycins
  作者：Bruno Drouillat、Olivia Poupardin、Yann Bourdreux、Christine Greck

  DOI：10.1016/s0040-4039(03)00460-x

  日期：2003.3

  The diastereoselective syntheses of the O-protected ribosyl-beta-hydroxy-alpha-amino esters 3 and 4, precursors of alpha-ribosyl-diazepanone core analogues of the liposidomycins, respectively, from the beta-ketoesters 5 and 6 are described. The anti relationship between the two adjacent aminated and hydroxylated carbons was controlled by sequential hydrogenation of the beta-ketoesters in the presence of chiral ruthenium catalysts and electrophilic amination of the resulting beta-hydroxyesters. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Efficient asymmetric synthesis of a functionalized Δ2-pyrazoline
  作者：Olivia Poupardin、Christine Greck、Jean Pierre Genet*

  DOI：10.1016/s0040-4039(00)01582-3

  日期：2000.11

  The first asymmetric synthesis of the (4S,SR)-5-carbomethoxy-4-hydroxy-Delta (2)-pyrazoline in four steps is described starting from the methyl 4,4-dimethoxy-3-oxobutanoate by sequential catalytic hydrogenation and electrophilic amination. (C) 2000 Elsevier Science Ltd. All rights reserved.