(R)-1-((3aS,4R,6aR)-6-Allyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol | 455251-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((3aS,4R,6aR)-6-Allyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol
• CAS: 455251-57-7
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: QPCKFRCQUTVEQO-DIGBMROFSA-N

反应信息

• 作为反应物：
  描述：

  (R)-1-((3aS,4R,6aR)-6-Allyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 在 sodium periodate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以82.3%的产率得到(3aR,4S,6aR)-6-Allyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde
  参考文献：
  名称：

  EASY SYNTHESIS OF 1-ALLYL-1-DEOXY-β- AND α- d-LYXOFURANOSES

  摘要：

  2,3;5,6-Di-O-isopropylidene-alpha-D-mannofuranosyl chloride reacted with allylmagnesium bromide with preferential inversion of the anomeric configuration to furnish a mixture of the 1-allyl-1-deoxy-beta- and alpha,D-mannofuranoses. Separation of beta and alpha derivatives was possible only after conversion to the 1-allyl-1-deoxylyxofuranoses 2 and 3. The beta configuration of the predominant product 2 was proved using the NOE method.

  DOI：

  10.1081/car-120003739
• 作为产物：
  描述：

  1-allyl-1-deoxy-2,3:5,6-di-O-isopropylidene-D-mannofuranose 在 硫酸 作用下， 以 甲醇 为溶剂， 以87%的产率得到(R)-1-((3aS,4R,6aR)-6-Allyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol
  参考文献：
  名称：

  EASY SYNTHESIS OF 1-ALLYL-1-DEOXY-β- AND α- d-LYXOFURANOSES

  摘要：

  2,3;5,6-Di-O-isopropylidene-alpha-D-mannofuranosyl chloride reacted with allylmagnesium bromide with preferential inversion of the anomeric configuration to furnish a mixture of the 1-allyl-1-deoxy-beta- and alpha,D-mannofuranoses. Separation of beta and alpha derivatives was possible only after conversion to the 1-allyl-1-deoxylyxofuranoses 2 and 3. The beta configuration of the predominant product 2 was proved using the NOE method.

  DOI：

  10.1081/car-120003739