(-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester | 893418-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester
• 英文别名: [(3R,4R)-4-hydroxy-4-methyl-5-oxooxolan-3-yl] acetate
• CAS: 893418-49-0
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: ZHCOVWDRKVQPPT-IYSWYEEDSA-N

物化性质

• 沸点：
  277.9±40.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (-)-(3R,4R)-β-(3,4-dimethoxyphenyl)acrylic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025
• 作为产物：
  描述：

  乙酸乙烯酯 、 2-methyl-2,3,4-trihydroxy-butanoic acid-1,4-lactone 在 Amano PS-1400 lipase 作用下， 以 正己烷 、 苯 为溶剂， 反应 96.0h， 以63%的产率得到(2S,3S)-2,3-dihydroxy-2-methyl-γ-butyrolactone
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025