(R)-3-acetyloxy-4-triphenylmethoxybutanenitrile | 890050-55-2

• 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-acetyloxy-4-triphenylmethoxybutanenitrile
• 英文别名: [(2R)-1-cyano-3-trityloxypropan-2-yl] acetate
• CAS: 890050-55-2
• 化学式: C₂₅H₂₃NO₃
• 分子量: 385.463
• InChiKey: IZQUNEMDNHPRBZ-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-acetyloxy-4-triphenylmethoxybutanenitrile 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (3R)-3-hydroxy-4-trityloxybutanenitrile
  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：

  三苯甲氧基甲基环氧乙烷 在 Pseudomonas cepacia lipase immobilized on ceramic particles 作用下， 以 乙醇 、 异丙醚 、 水 为溶剂， 反应 60.0h， 生成 (R)-3-acetyloxy-4-triphenylmethoxybutanenitrile
  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

文献信息

• Enantioconvergent chemoenzymatic synthesis of (R)-gamma-amino-beta-hydroxybutyric acid ((R)-GABOB)
  申请人：Kamal Ahmed

  公开号：US20060141606A1

  公开（公告）日：2006-06-29

  The present invention particularly relates to a chemoenzymatic process for the stereoselective preparation of both enantiomers of 3-hydroxy-4-trityloxy butanenitrile key intermediates for the preparation of (R)-GABOB by lipase mediated kinetic resolution of its racemates and their effective application in the enantioconvergent synthesis of (R)-GABOB.

  本发明特别涉及一种化学酶法过程，用于立体选择性制备3-羟基-4-三苄氧基丁腈的两个对映体，该中间体是通过脂肪酶介导的拆分其外消旋体制备(R)-GABOB的关键中间体，并且有效地应用于(R)-GABOB的对映体转化合成中。
• ENANTIOCONVERGENT CHEMOENZYMATIC SYNTHESIS OF (R)- GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID ((R) - GABOB)
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：EP1833977B1

  公开（公告）日：2009-04-29
• ENANTIOCONVERGENT CHEMOENZYMATIC SYNTHESIS OF (R)- GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID ((R) -GABOB)
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：EP1833977A1

  公开（公告）日：2007-09-19
• US7374926B2
  申请人：——

  公开号：US7374926B2

  公开（公告）日：2008-05-20
• [EN] ENANTIOCONVERGENT CHEMOENZYMATIC SYNTHESIS OF (R)- GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID ((R) -GABOB)<br/>[FR] SYNTHÈSE CHIMIOENZYMATIQUE ÉNANTIOCONVERGENTE DE L'ACIDE (R)-GAMMA-AMINO-BÊTA-HYDROXYBUTYRIQUE ((R)-GABOB)
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2006064513A1

  公开（公告）日：2006-06-22

  [EN] The present invention particularly relates to a chemoenzymatic process for the stereoselective preparation of both enantiomers of 3-hydroxy-4-trityloxy butanenitrile key intermediates for the preparation of (R)-GABOB by lipase mediated kinetic resolution of its racemates and their effective application in the enantioconvergent synthesis of (R)-GABOB.
  [FR] La présente invention concerne plus particulièrement un procédé chimioenzymatique permettant la synthèse stéréosélective des deux énantiomères du 3-hydroxy-4-trityloxybutanenitrile, qui sont les intermédiaires clés dans la synthèse du (R)-GABOB, par dédoublement cinétique assisté par une lipase d'un mélange racémique, ainsi que leur application proprement dite à la synthèse énantioconvergente du (R)-GABOB.