(2R,3S,3aS,6aR)-3-(benzyloxy)-2-methyl-5-methylenehexahydrofuro[3,2-b]furan | 1451180-62-3

• 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: (2R,3S,3aS,6aR)-3-(benzyloxy)-2-methyl-5-methylenehexahydrofuro[3,2-b]furan
• CAS: 1451180-62-3
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: GHMZOKMMWDKVDE-RZFFKMDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,3aS,6aR)-3-(benzyloxy)-2-methyl-5-methylenehexahydrofuro[3,2-b]furan 在 dirhodium tetraacetate 、 N-碘代丁二酰亚胺 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 C₁₈H₂₂O₆
  参考文献：
  名称：

  Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

  摘要：

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

  DOI：

  10.1021/ol402021e
• 作为产物：
  描述：

  dimethyltitanocene 、 3,6-anhydro-5-O-benzyl-2,7-di-deoxy-D-ido-heptono-2,4-lactone 以 甲苯 为溶剂， 以60%的产率得到(2R,3S,3aS,6aR)-3-(benzyloxy)-2-methyl-5-methylenehexahydrofuro[3,2-b]furan
  参考文献：
  名称：

  Ring-Contraction vs Ring-Expansion Reactions of Spiro-cyclopropanecarboxylated Sugars

  摘要：

  Electrophilic ring opening of spiro-cyclopropanecarboxylated sugars followed by reaction with DBU revealed interesting ring-contraction and ring-expansion reactions depending on the substrate and the kind of hydroxyl protective group present adjacent to the Spiro center. A stereoselective method for accessing a new class of carbon chain extended keto-furanoses and C-glycosylated bicyclic compounds is reported.

  DOI：

  10.1021/ol402021e