(1R)-1-acetoxy-3-O-acetyl-5-deoxy-4-O-formyl-1,2-O-isopropylidene-L-arabinitol | 1393110-61-6

• 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: (1R)-1-acetoxy-3-O-acetyl-5-deoxy-4-O-formyl-1,2-O-isopropylidene-L-arabinitol
• 英文别名: [(4R,5R)-5-[(1S,2S)-1-acetyloxy-2-formyloxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl] acetate
• CAS: 1393110-61-6
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: UWZMTWKUQOTBDZ-VKZDFBPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R)-1-acetoxy-3-O-acetyl-5-deoxy-4-O-formyl-1,2-O-isopropylidene-L-arabinitol 、 1-(4-bromophenyl)-1-(trimethylsilyloxy)ethylene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以89%的产率得到(1R)-3-O-acetyl-4-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(4-bromophenyl)ethyl]-5-deoxy-D-arabinitol
  参考文献：
  名称：

  Stereoselective Conversion of Sugar Derivatives into C-nucleosides

  摘要：

  A two-step process for the transformation of readily available carbohydrate derivatives into acyclic C-nucleosides is described. The carbohydrate undergoes a scission process that is followed by the addition of aryl ketone derivatives, allowing the introduction of a variety of aryl rings. The resulting acyclic C-nucleosides are transformed into 2-deoxy cyclic pyranosides in good yield and excellent stereoselectivity.

  DOI：

  10.1021/jo301031t
• 作为产物：
  描述：

  碘苯二乙酸 、 4-O-acetyl-2,3-O-isopropylidene-L-rhamnopyranose 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以91%的产率得到(1R)-1-acetoxy-3-O-acetyl-5-deoxy-4-O-formyl-1,2-O-isopropylidene-L-arabinitol
  参考文献：
  名称：

  Stereoselective Conversion of Sugar Derivatives into C-nucleosides

  摘要：

  A two-step process for the transformation of readily available carbohydrate derivatives into acyclic C-nucleosides is described. The carbohydrate undergoes a scission process that is followed by the addition of aryl ketone derivatives, allowing the introduction of a variety of aryl rings. The resulting acyclic C-nucleosides are transformed into 2-deoxy cyclic pyranosides in good yield and excellent stereoselectivity.

  DOI：

  10.1021/jo301031t