(R)-3-hydroxy-4-triphenylmethoxybutanamide | 913257-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (R)-3-hydroxy-4-triphenylmethoxybutanamide
• CAS: 913257-80-4
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: TWONBQKNUBYLDQ-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.55
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-4-triphenylmethoxybutanamide 在 吡啶 、 lead(IV) acetate 作用下， 以85%的产率得到(R)-5-triphenylmethoxymethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

  摘要：

  Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of beta-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure (R)-3-hydroxy-4-trityloxybutanenitrile and (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of (R)-GABOB. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.04.019
• 作为产物：
  描述：

  (R)-3-acetyloxy-4-triphenylmethoxybutanenitrile 在 ammonium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 以75%的产率得到(R)-3-hydroxy-4-triphenylmethoxybutanamide
  参考文献：
  名称：

  Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

  摘要：

  Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of beta-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure (R)-3-hydroxy-4-trityloxybutanenitrile and (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of (R)-GABOB. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.04.019