Boc-Chg-Gly(tBu)-OMe | 402958-93-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Chg-Gly(tBu)-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]-3,3-dimethylbutanoate
• CAS: 402958-93-4
• 化学式: C₂₀H₃₆N₂O₅
• 分子量: 384.516
• InChiKey: QDMCYNJJWJTOEN-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-Chg-Gly(tBu)-OMe 在 盐酸 、 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 (1S,3aR,6aS)-(2S)-2-环己基-N-(吡嗪基羰基)甘氨酰-3-甲基-L-缬氨酰八氢环戊二烯并[c]吡咯-1-羧酸乙酯
  参考文献：
  名称：

  P4 and P1′ optimization of bicycloproline P2 bearing tetrapeptidyl α-ketoamides as HCV protease inhibitors

  摘要：

  With the aim of improving HCV protease inhibitors reported in our previous manuscripts, we synthesized and evaluated a series of la-based tetrapeptidyl alpha-ketoamides with additional P4 modification. The promising analog discovered through this SAR, 5a, was further derivatized at P1' or P1 position. As a result of these efforts, we found that replacement of the P4 valine as seen in 1a with cyclohexylglycine (Chg) resulted in the discovery of 5a, 5c, and 5e endowed with improved cellular activity in comparison to 1a. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.007
• 作为产物：
  描述：

  L-叔亮氨酸甲酯盐酸盐 、 Boc-L-环己基甘氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到Boc-Chg-Gly(tBu)-OMe
  参考文献：
  名称：

  P4 and P1′ optimization of bicycloproline P2 bearing tetrapeptidyl α-ketoamides as HCV protease inhibitors

  摘要：

  With the aim of improving HCV protease inhibitors reported in our previous manuscripts, we synthesized and evaluated a series of la-based tetrapeptidyl alpha-ketoamides with additional P4 modification. The promising analog discovered through this SAR, 5a, was further derivatized at P1' or P1 position. As a result of these efforts, we found that replacement of the P4 valine as seen in 1a with cyclohexylglycine (Chg) resulted in the discovery of 5a, 5c, and 5e endowed with improved cellular activity in comparison to 1a. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.007

文献信息

• Azetidines and spiro azetidines as novel P2 units in hepatitis C virus NS3 protease inhibitors
  作者：Lavanya Bondada、Ramu Rondla、Ugo Pradere、Peng Liu、Chengwei Li、Drew Bobeck、Tamara McBrayer、Philip Tharnish、Jerome Courcambeck、Philippe Halfon、Tony Whitaker、Franck Amblard、Steven J. Coats、Raymond F. Schinazi

  DOI：10.1016/j.bmcl.2013.09.068

  日期：2013.12

  Herein, we report the synthesis and structure-activity relationship studies of new analogs of boceprevir 1 and telaprevir 2. Introduction of azetidine and spiroazetidines as a P2 substituent that replaced the pyrrolidine moiety of 1 and 2 led to the discovery of a potent hepatitis C protease inhibitor 37c (EC50 = 0.8 mu M). (C) 2013 Elsevier Ltd. All rights reserved.
• US7820671B2
  申请人：——

  公开号：US7820671B2

  公开（公告）日：2010-10-26
• [EN] PROCESS FOR PREPARATION OF INTERMEDIATES OF TELAPREVIR<br/>[FR] PROCÉDÉ DE PRÉPARATION D'INTERMÉDIAIRES DU TÉLAPRÉVIR
  申请人：REDDYS LAB LTD DR

  公开号：WO2014045263A2

  公开（公告）日：2014-03-27

  The present application relates to novel processes for preparation of (1S,3a R,6a S)-octahydrocyclopenta[c]pyrrole-1-carboxylic acid and its derivatives; and their use in preparation of Telaprevir.
• P4 and P1′ optimization of bicycloproline P2 bearing tetrapeptidyl α-ketoamides as HCV protease inhibitors
  作者：Yvonne Yip、Frantz Victor、Jason Lamar、Robert Johnson、Q. May Wang、John I. Glass、Nathan Yumibe、Mark Wakulchik、John Munroe、Shu-Hui Chen

  DOI：10.1016/j.bmcl.2004.07.007

  日期：2004.10

  With the aim of improving HCV protease inhibitors reported in our previous manuscripts, we synthesized and evaluated a series of la-based tetrapeptidyl alpha-ketoamides with additional P4 modification. The promising analog discovered through this SAR, 5a, was further derivatized at P1' or P1 position. As a result of these efforts, we found that replacement of the P4 valine as seen in 1a with cyclohexylglycine (Chg) resulted in the discovery of 5a, 5c, and 5e endowed with improved cellular activity in comparison to 1a. (C) 2004 Elsevier Ltd. All rights reserved.