(2S,3S)-2-Benzyl-1-(tert-butyloxycarbonyl)pyrrolidin-3-ol | 247578-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3S)-2-Benzyl-1-(tert-butyloxycarbonyl)pyrrolidin-3-ol
• 英文别名: tert-butyl (2S,3S)-2-benzyl-3-hydroxypyrrolidine-1-carboxylate；(2SR,3SR)-N-t-Butoxycarbonyl-2-benzyl-3-pyrrolidinol
• CAS: 247578-10-5
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: GOBHYMQCYUHPBS-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-Benzyl-1-(tert-butyloxycarbonyl)pyrrolidin-3-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Hydroxyoxazolidines as α-aminoacetaldehyde equivalents: Novel inhibitors of calpain

  摘要：

  The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropyl] carbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00391-1
• 作为产物：
  描述：

  (5S)-5-benzyl-4-hydroxy-1-t-butoxycarbonylpyrrol-2(5H)-one 在 sodium tetrahydroborate 、 dimethyl sulfide borane 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3S)-2-Benzyl-1-(tert-butyloxycarbonyl)pyrrolidin-3-ol
  参考文献：
  名称：

  Hydroxyoxazolidines as α-aminoacetaldehyde equivalents: Novel inhibitors of calpain

  摘要：

  The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropyl] carbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00391-1

文献信息

• [EN] PYRROLIDIN-3-YL COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] COMPOSES PYRROLIDIN-3-YLE UTILES EN TANT QU'INHIBITEURS DE LA BETA-SECRETASE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：MERCK & CO INC

  公开号：WO2006002004A1

  公开（公告）日：2006-01-05

  The present invention is directed to pyrrolidin-3-yl derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

  本发明涉及吡咯烷-3-基衍生物化合物，这些化合物是β-分泌酶的抑制剂，并且在治疗涉及β-分泌酶的疾病，如阿尔茨海默病中有用。该发明还涉及包含这些化合物的药物组合物，以及在治疗涉及β-分泌酶的这类疾病中使用这些化合物和组合物。
• Design of potential new HIV protease inhibitors: enantioconvergent synthesis of new pyrrolidin-3-ol, and pyrrolidin-3-one peptide conjugates
  作者：Jérôme Courcambeck、Frédéric Bihel、Céline De Michelis、Gilles Quéléver、Jean Louis Kraus

  DOI：10.1039/b101584m

  日期：——

  Novel potential HIV protease inhibitors are obtained by an enantioconvergent synthesis of mimicking Phe-Pro dipeptides, achieved through the coupling between Boc(L)Phe or Boc(L)Tyr and both enantiomers of syn-2-benzylpyrrolidin-3-ol and their corresponding pyrrolidin-3-one analogs. The stereochemistry and enantiopurity of intermediate 3-hydroxypyrrolidines 5a and 5b are determined through 1H NMR analysis, and through the synthesis and 19F NMR assignments of the corresponding Mosher’s esters 13a and 13b. The enantiopure compounds 5a and 5b are obtained with 100% diastereoselectivity using specific experimental reductive conditions upon Meldrum’s acid derivatives of activated aromatic amino acids.

  新型潜在的HIV蛋白酶抑制剂通过模仿苯丙氨酸-脯氨酸二肽的镜像收敛合成获得，该合成通过Boc(L)Phe或Boc(L)Tyr与syn-2-苯基吡咯烷-3-醇的两种对映体及其相应的吡咯烷-3-酮类似物之间的耦合实现。中间体3-羟基吡咯烷 5a 和 5b 的立体化学和对映体纯度通过1H NMR分析以及对应莫舍酯13a和13b的合成及19F NMR分析进行确认。使用特定的还原实验条件，在活化芳香氨基酸的梅尔德鲁姆酸衍生物上获得对映体纯化合物5a和5b，且实现了100%的非对映选择性。
• [EN] ATM KINASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE KINASE ATM ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：CHDI FOUNDATION INC

  公开号：WO2021113506A1

  公开（公告）日：2021-06-10

  Provided are certain ATM kinase inhibitors of Formula (I). Also provided herein are compositions of such compounds, and methods of their use.

  提供了某些Formula (I)的ATM激酶抑制剂。本文还提供了这些化合物的组合物，以及它们的使用方法。
• Hydroxyoxazolidines as α-aminoacetaldehyde equivalents: Novel inhibitors of calpain
  作者：Norton P. Peet、Hwa-Ok Kim、Angela L. Marquart、Michael R. Angelastro、Thaddeus R. Nieduzak、Julie N. White、Dirk Friedrich、Gary A. Flynn、Mark E. Webster、Roy J. Vaz、Matthew D. Linnik、Jack R. Koehl、Shujaath Mehdi、Philippe Bey、Bart Emary、Kin-Kai Hwang

  DOI：10.1016/s0960-894x(99)00391-1

  日期：1999.8

  The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropyl] carbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2. (C) 1999 Elsevier Science Ltd. All rights reserved.