2R,3S-4-Benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyric acid | 191408-25-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2R,3S-4-Benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyric acid
• 英文别名: (E,2R)-2-[(1S)-1-hydroxy-2-phenylmethoxyethyl]-5-phenylpent-4-enoic acid
• CAS: 191408-25-0
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: TXSXGMUTKHAANO-KASMDDHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2R,3S-4-Benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyric acid 在 palladium dihydroxide 、 palladium on activated charcoal 盐酸 、 ruthenium trichloride 、 sodium periodate 、 氢气 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester
  参考文献：
  名称：

  P1, P2′-Linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A novel series of 13- and 14-membered macrocyclic amines was developed by linking the P-1, and P-2, groups. The synthesis entails stereoselective Frater alkylation to install the anti-succinate configuration and macrocyclic amination via nucleophilic displacement. This strategy resulted in a new class of conformationally constrained inhibitors that are potent ind selective for MMP-8 and 9 over MMP-1 and 3. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00215-2
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 六甲基磷酰三胺 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四甲基乙二胺 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 2R,3S-4-Benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyric acid
  参考文献：
  名称：

  P1, P2′-Linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors

  摘要：

  A novel series of 13- and 14-membered macrocyclic amines was developed by linking the P-1, and P-2, groups. The synthesis entails stereoselective Frater alkylation to install the anti-succinate configuration and macrocyclic amination via nucleophilic displacement. This strategy resulted in a new class of conformationally constrained inhibitors that are potent ind selective for MMP-8 and 9 over MMP-1 and 3. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00215-2

文献信息

• US6281352B1
  申请人：——

  公开号：US6281352B1

  公开（公告）日：2001-08-28
• P1, P2′-Linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors
  作者：James J.-W. Duan、Lihua Chen、Chu-Biao Xue、Zelda R. Wasserman、Karl D. Hardman、Maryanne B. Covington、Robert R. Cope、Elizabeth C. Arner、Carl P. Decicco

  DOI：10.1016/s0960-894x(99)00215-2

  日期：1999.5

  A novel series of 13- and 14-membered macrocyclic amines was developed by linking the P-1, and P-2, groups. The synthesis entails stereoselective Frater alkylation to install the anti-succinate configuration and macrocyclic amination via nucleophilic displacement. This strategy resulted in a new class of conformationally constrained inhibitors that are potent ind selective for MMP-8 and 9 over MMP-1 and 3. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.