(3S,4S,4aS,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-acetoxy-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one | 1039034-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S,4aS,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-acetoxy-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one
• CAS: 1039034-56-4
• 化学式: C₂₂H₃₀O₇
• 分子量: 406.476
• InChiKey: GBLPVFFYCBTWPB-JIVYVDHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,4aS,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-acetoxy-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99%的产率得到(3S,4S,4aS,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-acetoxy-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
• 作为产物：
  描述：

  (3S,4S,4aR,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-hydroxy-7-(4-methoxybenzyloxy)-3,4a,6,8-tetramethylpyrano[3,2-b]pyran-2(3H)-one 、 乙酸酐 在 吡啶 作用下， 反应 7.0h， 以80%的产率得到(3S,4S,4aS,6S,7R,8R,8aS)-3,4,4a,7,8,8a-hexahydro-4-acetoxy-7-(4-methoxybenzyloxy)-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