(1R)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(4-methoxyphenyl)ethyl]-D-erythritol | 1393110-76-3

• 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-(4-methoxyphenyl)ethyl]-D-erythritol
• 英文别名: [(2R)-2-formyloxy-2-[(4S,5R)-5-[2-(4-methoxyphenyl)-2-oxoethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl] benzoate
• CAS: 1393110-76-3
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: LMFAJWKOQMAPQN-VSKRKVRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(4-methoxyphenyl)ethyl]-D-erythritol 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 以94%的产率得到(1R)-4-O-benzoyl-1,2-O-isopropylidene-1-[2-oxo-2-(4-methoxyphenyl)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
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 (1R)-4-O-benzoyl-3-O-formyl-1,2-O-isopropylidene-1-[2-oxo-2-(4-methoxyphenyl)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.