(4aR,6S,7R,8R,8as)-4a,7,8,8a-tetrahydro-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2-one | 1039034-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (4aR,6S,7R,8R,8as)-4a,7,8,8a-tetrahydro-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2-one
• 英文别名: (4aR,6S,7R,8R,8aS)-7-hydroxy-3,4a,6,8-tetramethyl-6,7,8,8a-tetrahydropyrano[3,2-b]pyran-2-one
• CAS: 1039034-47-3
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: DSJDRWWEGSUMQS-RACFRTOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(E)-4-(tert-butyldimethylsiloxy)-2-octenoic acid 、 (4aR,6S,7R,8R,8as)-4a,7,8,8a-tetrahydro-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2-one 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.33h， 以92%的产率得到(2S,3R,4R,4aS,8aR)-2,4,7,8a-tetramethyl-6-oxo-2,3,4,4a,6,8a-hexahydropyrano[3,2-b]pyran-3-yl (S,E)-4-((tert-butyldimethylsilyl)oxy)oct-2-enoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y
• 作为产物：
  描述：

  (4aR,6S,7R,8R,8aS)-4a,7,8,8a-tetrahydro-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85%的产率得到(4aR,6S,7R,8R,8as)-4a,7,8,8a-tetrahydro-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y