(3S,4S,4aS,6S,7R,8R,8aS)-4,4a,6,7,8,8a-hexahydro-4-triethylsiloxy-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one | 1039034-59-7

• 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: (3S,4S,4aS,6S,7R,8R,8aS)-4,4a,6,7,8,8a-hexahydro-4-triethylsiloxy-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one
• 英文别名: (2S,3R,4R,4aS,7S,8S,8aS)-3-hydroxy-2,4,7,8a-tetramethyl-8-triethylsilyloxy-2,3,4,4a,7,8-hexahydropyrano[3,2-b]pyran-6-one
• CAS: 1039034-59-7
• 化学式: C₁₈H₃₄O₅Si
• 分子量: 358.55
• InChiKey: IMJYEHNLSYQLRO-CRJFESBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(E)-4-(tert-butyldimethylsiloxy)-2-octenoic acid 、 (3S,4S,4aS,6S,7R,8R,8aS)-4,4a,6,7,8,8a-hexahydro-4-triethylsiloxy-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-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 11.17h， 以78%的产率得到(2S,3R,4R,4aS,7S,8S,8aS)-2,4,7,8a-tetramethyl-6-oxo-8-((triethylsilyl)oxy)octahydropyrano[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：

  (3S,4S,4aS,6S,7R,8R,8aS)-4,4a,6,7,8,8a-hexahydro-4-triethylsiloxy-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-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84%的产率得到(3S,4S,4aS,6S,7R,8R,8aS)-4,4a,6,7,8,8a-hexahydro-4-triethylsiloxy-7-hydroxy-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-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

文献信息

• Asymmetric Total Synthesis of Botcinins C, D, and F
  作者：Hiroki Fukui、Isamu Shiina

  DOI：10.1021/ol801066y

  日期：2008.7.17

  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.