(1R)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(biphenyl-4-yl)ethyl]-D-erythritol | 1393110-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(biphenyl-4-yl)ethyl]-D-erythritol
• 英文别名: [(2R)-2-[(4S,5R)-2,2-dimethyl-5-[2-oxo-2-(4-phenylphenyl)ethyl]-1,3-dioxolan-4-yl]-2-formyloxyethyl] benzoate
• CAS: 1393110-79-6
• 化学式: C₂₉H₂₈O₇
• 分子量: 488.537
• InChiKey: BZKSTIRIYPCJRG-PFBJBMPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(biphenyl-4-yl)ethyl]-D-erythritol 在 sodium tetrahydroborate 、 碳酸氢钠 、 乙酸乙酯 作用下， 以 甲醇 为溶剂， 反应 1.58h， 以81%的产率得到4-O-benzoyl-1-[2-hydroxy-2-(biphenyl-4-yl)ethyl]-1,2-O-isopropylidene-D-erythritol
  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：

  联苯单乙酮 、 1-acetoxy-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene derythritol 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 反应 3.33h， 以67%的产率得到(1R)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(biphenyl-4-yl)ethyl]-D-erythritol
  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

文献信息

• Stereoselective Conversion of Sugar Derivatives into <i>C</i>-nucleosides
  作者：Javier Miguélez、Venkateswara Rao Batchu、Alicia Boto

  DOI：10.1021/jo301031t

  日期：2012.9.7

  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.