(1S,4S,5S,6S,7R)-6,7-(carbonyldioxy)-1-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one | 214259-45-7

• 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: (1S,4S,5S,6S,7R)-6,7-(carbonyldioxy)-1-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
• 英文别名: [(1S,2R,6S,7S,8S)-1-methyl-4,10-dioxo-3,5,9-trioxatricyclo[5.3.0.02,6]decan-8-yl]methyl 2,2-dimethylpropanoate
• CAS: 214259-45-7
• 化学式: C₁₄H₁₈O₇
• 分子量: 298.293
• InChiKey: WIZVMBFQEWZVOP-DHGLKCJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,4S,5S,6S,7R)-6,7-(carbonyldioxy)-1-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以45%的产率得到2,2-Dimethyl-propionic acid (3aS,4S,6S,6aS)-6-hydroxy-6a-methyl-2-oxo-hexahydro-furo[3,4-b]furan-4-ylmethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of [3.3.0]‐Fused γ‐Butyrolactones of Carbohydrates

  摘要：

  A facile and stereoselective method is described for the preparation of fused 2,3-gamma-butyrolactones of lyxofuranose from the unexpected rearrangement in basic media of the photocycloadduct between homochiral 2(5H)-furanones and vinylene carbonate.

  DOI：

  10.1081/car-120026454
• 作为产物：
  描述：

  2-methyl-5-pivaloyloxymethyl-4-oxatricyclo[5.2.1.0^2,6]dec-8-en-3-one 以 丙酮 、 苯 为溶剂， 反应 200.0h， 生成 (1S,4S,5S,6S,7R)-6,7-(carbonyldioxy)-1-methyl-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of [3.3.0]‐Fused γ‐Butyrolactones of Carbohydrates

  摘要：

  A facile and stereoselective method is described for the preparation of fused 2,3-gamma-butyrolactones of lyxofuranose from the unexpected rearrangement in basic media of the photocycloadduct between homochiral 2(5H)-furanones and vinylene carbonate.

  DOI：

  10.1081/car-120026454

文献信息

• Facile and stereoselective synthesis of fused γ-butyrolactones of carbohydrates
  作者：Anna Gregori、Ramón Alibés、JoséLuis Bourdelande、Josep Font

  DOI：10.1016/s0040-4039(98)01477-4

  日期：1998.9

  Photocycloadducts obtained from different homochiral butenolides and vinylene carbonate are shown to be useful precursors of fused gamma-butyrolactones of carbohydrates. (C) 1998 Elsevier Science Ltd. All rights reserved.