3-hydroxy-4-triphenylmethoxybutanenitrile | 890050-54-1

• 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: 3-hydroxy-4-triphenylmethoxybutanenitrile
• 英文别名: (+/-)-3-Hydroxy-4-trityloxybutane-nitrile；3-hydroxy-4-trityloxybutanenitrile
• CAS: 890050-54-1
• 化学式: C₂₃H₂₁NO₂
• 分子量: 343.425
• InChiKey: LFABBSDQLOSVRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-triphenylmethoxybutanenitrile 在 ammonium hydroxide 、 Pseudomonas cepacia lipase immobilized on ceramic particles 、 双氧水 作用下， 以 乙醇 、 异丙醚 为溶剂， 反应 60.0h， 生成 (S)-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
• 作为产物：
  描述：

  三苯甲氧基甲基环氧乙烷 、 氰化钠 以 乙醇 、 水 为溶剂， 以82%的产率得到3-hydroxy-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)-γ-amino-β-hydroxybutyric acid ((R)-GABOB)
  申请人：Council of Scientific and Industrial Research

  公开号：US07374926B2

  公开（公告）日：2008-05-20

  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酶过程，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其外消旋体的动力学分辨制备(R)-GABOB的制备的关键中间体，并且它们在(R)-GABOB的对映体转化合成中的有效应用。
• Process for the production of 3,5,6-trihydroxyhexanoic acid derivative
  申请人：Kanegafuchi Chemical Industry Co., Ltd.

  公开号：EP0374922A2

  公开（公告）日：1990-06-27

  A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: wherein P¹ and P² are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of: reacting a butyronitrile derivative of the formula: wherein P¹ and P² are the same as defined above with an α-haloacetate of the formula: X-CH₂-COOR      (III) wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: wherein P¹, P² and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).

  一种式 3，5，6-三羟基己酸衍生物化合物： 其中 P¹ 和 P² 独立地为氢原子或羟基保护基团，或共同形成一个环，且 R 为烷基，可通过包括以下步骤的工艺有效地制备： 使以下式子的丁腈衍生物反应 式中 P¹ 和 P² 与上式定义相同的α-卤代乙酸酯反应： x-ch₂-coor (iii) 其中 X 为卤素原子，R 与上式所定义的相同，在选自锌和锌-铜组成的金属催化剂存在下，生成式如下的酮酸衍生物： 其中 P¹、P² 和 R 与上述定义相同，以及 然后还原得到的式 (IV) 酮酸衍生物。
• 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