(2R,3S,4R,5R)-2-<(4S)-1,3-Dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-4,5-(methylenedioxy)-2H-pyran-6-one | 150254-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2R,3S,4R,5R)-2-<(4S)-1,3-Dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-4,5-(methylenedioxy)-2H-pyran-6-one
• CAS: 150254-48-1
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: LSPBSAJPNABHBL-XVPYXCLNSA-N

物化性质

• 沸点：
  367.5±42.0 °C(predicted)
• 密度：
  1.264±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2-<(4S)-1,3-Dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-4,5-(methylenedioxy)-2H-pyran-6-one 在 硫酸 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 Sodium; (4R,5R)-4,5-dimethyl-5-((1S,2R,3S)-2,3,4-trihydroxy-1-methyl-butyl)-[1,3]dioxolane-4-carboxylate
  参考文献：
  名称：

  Synthetic studies on macropyrrolizidine alkaloid, monocrotaline: enantioselective synthesis of a necic acid moiety, monocrotalic acid methylene acetal

  摘要：

  A methylene acetal derivative 4 of the necic acid, monocrotalic acid, part of the macropyrrolizidine alkaloid, monocrotaline, was enantioselectively synthesized from 2-furylmethanol derivative 6. Oxidation of 6, followed by silylation of the resulting lactol 9, gave silyl ether 19 as a major product. Introduction of the di-tert-hydroxy groups to 22 was achieved by stereoselective dihydroxylation with osmium tetroxide. After protection of the vicinal diol as a methylenedioxy derivative, acetal 26 was successfully converted into the desired product 4.

  DOI：

  10.1021/jo00068a022
• 作为产物：
  描述：

  (2R,3S,4R,5R)-2-<(4S)-1,3-Dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-4,5-(methylenedioxy)-2H-pyran-6-ol 在 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到(2R,3S,4R,5R)-2-<(4S)-1,3-Dioxolan-4-yl>-3,4,5,6-tetrahydro-3,4,5-trimethyl-4,5-(methylenedioxy)-2H-pyran-6-one
  参考文献：
  名称：

  Synthetic studies on macropyrrolizidine alkaloid, monocrotaline: enantioselective synthesis of a necic acid moiety, monocrotalic acid methylene acetal

  摘要：

  A methylene acetal derivative 4 of the necic acid, monocrotalic acid, part of the macropyrrolizidine alkaloid, monocrotaline, was enantioselectively synthesized from 2-furylmethanol derivative 6. Oxidation of 6, followed by silylation of the resulting lactol 9, gave silyl ether 19 as a major product. Introduction of the di-tert-hydroxy groups to 22 was achieved by stereoselective dihydroxylation with osmium tetroxide. After protection of the vicinal diol as a methylenedioxy derivative, acetal 26 was successfully converted into the desired product 4.

  DOI：

  10.1021/jo00068a022