(+/-)-2,3-di-O-acetyl-2-C-methyl-D-erythrono-1,4-lactone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-2,3-di-O-acetyl-2-C-methyl-D-erythrono-1,4-lactone
• 英文别名: (4-Acetyloxy-4-methyl-5-oxooxolan-3-yl) acetate
• 化学式: C₉H₁₂O₆
• 分子量: 216.191
• InChiKey: WFOCCZCFZZOAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-2,3-di-O-acetyl-2-C-methyl-D-erythrono-1,4-lactone 在 Amano PS-1400 lipase 、 potassium carbonate 、 sodium phosphate 作用下， 以 甲醇 、 水 、 Petroleum ether 、 苯 为溶剂， 反应 36.0h， 生成 (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
• 作为产物：
  描述：

  乙酸酐 、 2-methyl-2,3,4-trihydroxy-butanoic acid-1,4-lactone 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 5.0h， 以90%的产率得到(+/-)-2,3-di-O-acetyl-2-C-methyl-D-erythrono-1,4-lactone
  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

文献信息

• 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
  作者：Sanjib Gogoi、Narshinha P. Argade

  DOI：10.1016/j.tetasy.2006.02.025

  日期：2006.3

  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.