(3aR,4R,5S,7aS)-4-acetoxy-1,3,3a,4,5,7a-hexahydro-2-benzofuran-5-yl acetate | 1094000-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,4R,5S,7aS)-4-acetoxy-1,3,3a,4,5,7a-hexahydro-2-benzofuran-5-yl acetate
• 英文别名: [(3aR,4R,5S,7aS)-4-acetyloxy-1,3,3a,4,5,7a-hexahydro-2-benzofuran-5-yl] acetate
• CAS: 1094000-10-8
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: SCHYJNLFJYJPGY-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酸酐 、 乙酸乙烯酯 、 (+/-)-(3aS,4S,5R,7aR)-1,3,3a,4,5,7a-hexahydro-2-benzofuran-4,5-diol 在 Candida antarctica lipase 、 吡啶 作用下， 反应 24.0h， 生成 (3aR,4R,5S,7aS)-4-acetoxy-1,3,3a,4,5,7a-hexahydro-2-benzofuran-5-yl acetate 、 (+/-)-(3aS,4S,5R,7aR)-4-acetoxy-1,3,3a,4,5,7a-hexahydro-2-benzofuran-5-yl acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Bishomo-inositols as Glycosidase Inhibitors

  摘要：

  For the synthesis of various bishomo-inositol derivatives, 1,3,3a,7a-tetrahydro-2-benzofuran was used as the key compound. For further functionalization of the diene unit, the diene was subjected to photooxygenation, epoxidation, and cis-hydroxylation reactions. The endoperoxide linkage was cleaved by thiourea. The remaining double bond was subjected to epoxidation and cis-hydroxylation reactions. The epoxide rings and tetrahydrofuran rings formed were opened by acid-catalyzed reaction with sulfamic acid. The combination of these reactions resulted in the formation of various new inositol derivatives such as bishomo-chiro-inositol, bishomo-myo-inositol, and two isomeric bishomo-allo-inositols.

  DOI：

  10.1021/jo801344f