(2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate | 128360-00-9

• 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: (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate
• 英文别名: (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-hydroxypyrrolidine-1,2-dicarboxylate；2-O-methyl 1-O-(2-trimethylsilylethyl) (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 128360-00-9
• 化学式: C₁₂H₂₃NO₅Si
• 分子量: 289.404
• InChiKey: JTYAIKIZAXMCHR-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 在 三氟甲磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 17.0h， 生成 (2S,4S)-Methyl 4-acetoxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Selective transformation of O-2-(trimethylsilyl)ethyl and O-tert-butyl carbamates into O-benzyl carbamates using benzyl trichloroacetimidate

  摘要：

  DOI：

  10.1021/jo00304a035
• 作为产物：
  描述：

  L-羟基脯氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Total syntheses of bulgecinine and bulgecin C from (2S,4R)-hydroxyproline

  摘要：

  DOI：

  10.1021/jo00305a007

文献信息

• Hepatitis C Virus Inhibitors
  申请人：Hiebert Sheldon

  公开号：US20100080770A1

  公开（公告）日：2010-04-01

  Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  揭示了一类具有一般式的丙型肝炎病毒抑制剂。还揭示了包含这些化合物的组合物以及使用这些化合物抑制HCV的方法。
• Electrochemical oxidation of proline derivatives: total syntheses of bulgecinine and bulgecin C
  作者：Anthony G. M. Barrett、Daniel Pilipauskas

  DOI：10.1021/jo00008a040

  日期：1991.4

  The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.
• The discovery and optimization of naphthalene-linked P2-P4 Macrocycles as inhibitors of HCV NS3 protease
  作者：Michael Bowsher、Sheldon Hiebert、Rongti Li、Alan X. Wang、Jacques Friborg、Fei Yu、Dennis Hernandez、Ying-Kai Wang、Herbert Klei、Ramkumar Rajamani、Kathy Mosure、Jay O. Knipe、Nicholas A. Meanwell、Fiona McPhee、Paul M. Scola

  DOI：10.1016/j.bmcl.2017.11.005

  日期：2018.1

  Naphthalene-linked P2-P4 macrocycles within a tri-peptide-based acyl sulfonamide chemotype have been synthesized and found to inhibit HCV NS3 proteases representing genotypes 1a and 1b with single digit nanomolar potency. The pharmacokinetic profile of compounds in this series was optimized through structural modifications along the macrocycle tether as well as the P1 subsite. Ultimately a compound with oral bioavailability of 100% in rat, and a long half-life in plasma was obtained. However, compounds in this macrocyclic series exhibited cardiac effects in an isolated rabbit heart model and for this reason further optimization efforts were discontinued. (C) 2017 Elsevier Ltd. All rights reserved.
• BARRETT, ANTHONY G. M.;PILIPAUSKAS, DANIEL, J. ORG. CHEM., 55,(1990) N7, C. 5170-5173
  作者：BARRETT, ANTHONY G. M.、PILIPAUSKAS, DANIEL

  DOI：——

  日期：——