(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-(2-oxo-1-oxa-3-azacyclotetradecan-3-yl)-1-phenylbutan-2-yl]carbamate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-(2-oxo-1-oxa-3-azacyclotetradecan-3-yl)-1-phenylbutan-2-yl]carbamate
• 英文别名: [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-3-hydroxy-4-(2-oxo-1-oxa-3-azacyclotetradec-3-yl)-1-phenylbutan-2-yl]carbamate
• 化学式: C₂₉H₄₄N₂O₇
• 分子量: 532.678
• InChiKey: KEKJFJPYOLOXEK-UIPNDDLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane 在 palladium on activated charcoal titanium(IV) isopropylate 、 Cl₂(PCy₃)2=CHPh 、 水 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 20.0h， 生成 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-(2-oxo-1-oxa-3-azacyclotetradecan-3-yl)-1-phenylbutan-2-yl]carbamate
  参考文献：
  名称：

  Novel cyclourethane-Derived HIV protease inhibitors: A ring-closing olefin metathesis based strategy

  摘要：

  A series of novel macrocyclic urethanes incorporating a (R)-hydroxyethylamine isostere was designed and synthesized. Ring size and substituent efffects have been investigated. Cyclourethanes containing 14- to 16-membered rings exhibited low nanomolar inhibitory potencies against HIV-1 protease. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00300-1

文献信息

• Novel cyclourethane-Derived HIV protease inhibitors: A ring-closing olefin metathesis based strategy
  作者：Arun K Ghosh、Lisa M Swanson、Chunfeng Liu、Khaja Azhar Hussain、Hanna Cho、D.Eric Walters、Louis Holland、Jim Buthod

  DOI：10.1016/s0960-894x(02)00300-1

  日期：2002.8

  A series of novel macrocyclic urethanes incorporating a (R)-hydroxyethylamine isostere was designed and synthesized. Ring size and substituent efffects have been investigated. Cyclourethanes containing 14- to 16-membered rings exhibited low nanomolar inhibitory potencies against HIV-1 protease. (C) 2002 Elsevier Science Ltd. All rights reserved.