(2S,5S,3E)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-{[(1,1-dimethylethoxy)carbonyl]-N-benzyl}amino-1,6-diphenylhex-3-ene | 168846-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,5S,3E)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-{[(1,1-dimethylethoxy)carbonyl]-N-benzyl}amino-1,6-diphenylhex-3-ene
• 英文别名: tert-butyl benzyl((2S,5S,E)-5-((tert-butoxycarbonyl)amino)-1,6-diphenylhex-3-en-2-yl)carbamate；tert-butyl N-benzyl-N-[(E,2S,5S)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-1,6-diphenylhex-3-en-2-yl]carbamate
• CAS: 168846-63-7
• 化学式: C₃₅H₄₄N₂O₄
• 分子量: 556.745
• InChiKey: MHENLUKFXFRHBZ-QBYLACLOSA-N

物化性质

• 沸点：
  674.9±55.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S,3E)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-{[(1,1-dimethylethoxy)carbonyl]-N-benzyl}amino-1,6-diphenylhex-3-ene 在 palladium on activated charcoal 氢气 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 氨 为溶剂， -33.0~20.0 ℃ 、310.26 kPa 条件下， 反应 7.0h， 生成 (1R,4R)-N-(1-benzyl-4-benzyloxycarbonylamino-5-phenylpentyl)-t-butylcarbamate
  参考文献：
  名称：

  Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors

  摘要：

  The Julia's olefination reaction between the sulfone derivative (10) and the aldehyde (13) (both obtained from L-phenylalanine) followed by debenzylation led to the formation (2S,5S,3E)-2,5-bis-[( I,l-dimethyl ethoxy)-carbonyl]amino-l ,6-diphenylhex-3-ene (4a). Similarly (2S,5S,3E)-2,5-bis- [(1,1-dimethylethoxy)-carbonyl]amino- 1-phenyl-6-(p-methoxy)phenylhex-3-ene (4b) was also synthesised from the sulfone (10) and L-tyrosine derived aldehyde (21). These novel intermediates (4a and 4b) were subjected to epoxidation, hydrogenation, hydroboration-oxidation and dihydroxylation reactions. These modifications resulted in the synthesis of known and unknown, C-2-symmetric and pseudo-C-2-symmetric diamino-epoxides, dideoxy derivatives, diols and deoxy diols based HIV protease inhibitors. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00160-9
• 作为产物：
  描述：

  N-benzyl-N-(tert-butoxycarbonyl)-L-phenylalaninal 在 吡啶 、 disodium hydrogenphosphate 、 正丁基锂 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 (2S,5S,3E)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-{[(1,1-dimethylethoxy)carbonyl]-N-benzyl}amino-1,6-diphenylhex-3-ene
  参考文献：
  名称：

  Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors

  摘要：

  The Julia's olefination reaction between the sulfone derivative (10) and the aldehyde (13) (both obtained from L-phenylalanine) followed by debenzylation led to the formation (2S,5S,3E)-2,5-bis-[( I,l-dimethyl ethoxy)-carbonyl]amino-l ,6-diphenylhex-3-ene (4a). Similarly (2S,5S,3E)-2,5-bis- [(1,1-dimethylethoxy)-carbonyl]amino- 1-phenyl-6-(p-methoxy)phenylhex-3-ene (4b) was also synthesised from the sulfone (10) and L-tyrosine derived aldehyde (21). These novel intermediates (4a and 4b) were subjected to epoxidation, hydrogenation, hydroboration-oxidation and dihydroxylation reactions. These modifications resulted in the synthesis of known and unknown, C-2-symmetric and pseudo-C-2-symmetric diamino-epoxides, dideoxy derivatives, diols and deoxy diols based HIV protease inhibitors. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00160-9

文献信息

• [EN] METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION D'AGENTS PHARMACEUTIQUES
  申请人：GILEAD SCIENCES INC

  公开号：WO2013116715A1

  公开（公告）日：2013-08-08

  Methods and intermediates useful for preparing a compound of formula I and salts thereof.

  用于制备式I化合物及其盐的方法和中间体。
• MODULATORS OF PHARMACOKINETIC PROPERTIES OF THERAPEUTICS
  申请人：Desai Manoj C.

  公开号：US20100189687A1

  公开（公告）日：2010-07-29

  The present application provides for a compound of Formula IV, or a pharmaceutically acceptable salt, solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods and include the administration of such compounds with at least one additional therapeutic agent.

  本申请提供了公式IV的化合物，或其药学上可接受的盐，溶剂化合物和/或酯，含有这些化合物的组合物，包括给予这些化合物的治疗方法，以及包括给予这些化合物和至少一种额外治疗药物的治疗方法。
• WO2008/10921
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of a novel C2-symmetrical (2S,5S)-2,5-bis-[(1,1-dimethylethoxy)carbonylamino]-1,6-diphenylhex-3-ene: Applications in the synthesis of potential HIV protease inhibitors
  作者：AV Rama Rao、Mukund K Gurjar、Shashwati Pal、Richard J Pariza、Mukund S Chorghade

  DOI：10.1016/0040-4039(95)00255-b

  日期：1995.4
• Modulators of pharmacokinetic properties of therapeutics
  申请人：GILEAD SCIENCES, INC.

  公开号：EP2487162B1

  公开（公告）日：2016-08-17