(S)-3-hydroxy-4-triphenylmethoxybutanamide | 330555-58-3

• 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: (S)-3-hydroxy-4-triphenylmethoxybutanamide
• 英文别名: (S)-3-hydroxy-4-(trityloxy)butanamide；(S)-3-hydroxy-4-(trityloxy)butyramide；(S)-4-trityloxy-3-hydroxybutyramide；(S)-3-Hydroxy-4-trityloxy butyramide；(S)-3-hydroxy-4-trityloxy butanamide；(3S)-3-hydroxy-4-trityloxybutanamide
• CAS: 330555-58-3
• 化学式: C₂₃H₂₃NO₃
• 分子量: 361.441
• InChiKey: TWONBQKNUBYLDQ-NRFANRHFSA-N

物化性质

• 熔点：
  107.5-108.5 °C
• 沸点：
  578.1±50.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-hydroxy-4-triphenylmethoxybutanamide 在 sodium hydroxide 、 sodium hypochlorite 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 16.0h， 生成 (S)-3-(2,5-dimethoxyphenacyl)-5-trityloxymethyl-2-oxazolidinone
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF OXAZOLIDINONES AND METHOD OF USE THEREOF
  [FR] PROCEDE POUR L'ELABORATION D'OXAZOLIDINONES ET PROCEDE D'UTILISATION CORRESPONDANT

  摘要：

  公开号：

  WO2003106413A3
• 作为产物：
  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

文献信息

• Gold(I)-catalyzed, one-pot, oxidative formation of 2,4-disubstituted thiazoles: Application to the synthesis of a pateamine-related macrodiolide
  作者：Tao Xu、Claire Cuyamendous、Sarah L. Brown、Sarah K. Andreassend、Hemi Cumming、Gary B. Evans、Paul H. Teesdale-Spittle、Joanne E. Harvey

  DOI：10.1016/j.tet.2021.132109

  日期：2021.5

  Thiazoles are important heterocyclic motifs in many target molecules. Extension of a reported gold(I)-catalyzed oxidative coupling of alkynes and thioamides to the synthesis of functionalized thiazole-containing products is presented, including the compatibility of this reaction with ester, protected hydroxyl, alkene and thioether groups. The utility of this one-pot process is demonstrated in the preparation

  噻唑是许多靶分子中重要的杂环基序。提出了已报道的炔烃和硫代酰胺的金（I）催化的氧化偶联至官能化的含噻唑产物的合成，包括该反应与酯，被保护的羟基，烯烃和硫醚基团的相容性。一锅法的实用性在制备简化的帕他命A类似物的含噻唑的大环氧化物中得到了证明。
• New Synthesis of Chiral 1,3-Oxazinan-2-ones from Carbohydrate Derivatives
  作者：Jean-Rene Ella-Menye、Vibha Sharma、Guijun Wang

  DOI：10.1021/jo040224q

  日期：2005.1.1

  Chiral 1,3-oxazinan-2-ones are useful intermediates in synthesizing pharmaceutical compounds and amino alcohols. In this paper, we report a new synthetic method to chiral 6-hydroxymethyl 1,3-oxazinan-2-ones and their analogues from carbohydrate derivatives. The synthesis was accomplished by the reaction of optically pure 3-hydroxy-γ-butyrolactone with a primary amine to give an amide, which was reduced

  手性的1，3-恶二酮-2-酮是合成药物化合物和氨基醇的有用中间体。在本文中，我们报告了一种从碳水化合物衍生物中合成手性6-羟甲基1,3-恶二嗪-2-酮及其类似物的新方法。合成是通过光学纯的3-羟基-γ-丁内酯与伯胺反应生成酰胺，将其还原并羰基化得到所需化合物类别。
• 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。
• [EN] FUSED QUADRACYCLIC COMPOUNDS, COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSÉS QUADRACYCLIQUES FUSIONNÉS, COMPOSITIONS ET LEURS UTILISATIONS
  申请人：TABOMEDEX BIOSCIENCES INC

  公开号：WO2022150707A1

  公开（公告）日：2022-07-14

  Provided herein are substituted fused quadracyclic compounds useful as inhibitors of MK2. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention also provides medical uses of substituted fused quadracyclic compounds.

  本发明提供了用作MK2抑制剂的取代融合四环化合物。该发明还提供了该化合物的制药组合物。该发明还提供了取代融合四环化合物的医药用途。