(3aS,5S,9bS)-8-Methoxy-5-methyl-7-phenyl-2-triisopropylsilanyloxy-3,3a,5,9b-tetrahydro-2H-furo[3,2-c]isochromene-6,9-diol | 1059606-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3aS,5S,9bS)-8-Methoxy-5-methyl-7-phenyl-2-triisopropylsilanyloxy-3,3a,5,9b-tetrahydro-2H-furo[3,2-c]isochromene-6,9-diol
• 英文别名: (3aS,5S,9bS)-8-methoxy-5-methyl-7-phenyl-2-tri(propan-2-yl)silyloxy-3,3a,5,9b-tetrahydro-2H-furo[3,2-c]isochromene-6,9-diol
• CAS: 1059606-40-4
• 化学式: C₂₈H₄₀O₆Si
• 分子量: 500.707
• InChiKey: XOBBGTHVZONGCZ-IPPKLLHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.21
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,5S,9bS)-8-Methoxy-5-methyl-7-phenyl-2-triisopropylsilanyloxy-3,3a,5,9b-tetrahydro-2H-furo[3,2-c]isochromene-6,9-diol 在 盐酸 、 pyridinium chlorochromate 作用下， 生成 (3aS,5S,9bS)-8-Methoxy-5-methyl-7-phenyl-3,3a,5,9b-tetrahydro-furo[3,2-c]isochromene-2,6,9-trione
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004
• 作为产物：
  描述：

  4-Hydroxy-3-methoxy-4-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-2-phenyl-cyclobut-2-enone 以 甲苯 为溶剂， 生成 (3aS,5S,9bS)-8-Methoxy-5-methyl-7-phenyl-2-triisopropylsilanyloxy-3,3a,5,9b-tetrahydro-2H-furo[3,2-c]isochromene-6,9-diol
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004

文献信息

• General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D
  作者：Michael P. Winters、Michael Stranberg、Harold W. Moore

  DOI：10.1021/jo00104a004

  日期：1994.12

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.