(2S,5S,3E)-2,5-bis[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-3-ene | 189456-83-5

• 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)-2,5-bis[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-3-ene
• 英文别名: tert-butyl N-[(E,2S,5S)-1-(4-methoxyphenyl)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-3-en-2-yl]carbamate
• CAS: 189456-83-5
• 化学式: C₂₉H₄₀N₂O₅
• 分子量: 496.647
• InChiKey: GIBJUDIVELPEKQ-KDBREVJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S,3E)-2,5-bis[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-3-ene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以65%的产率得到(2S,3R,4R,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1-phenyl-6-(p-methoxy)phenyl-3,4-epoxyhexane
  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：

  (S)-2-Benzylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester 在 吡啶 、 disodium hydrogenphosphate 、 锂硼氢 、 正丁基锂 、 sodium amalgam 、 sodium 、 三氧化硫吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氨 、 水 、 二甲基亚砜 为溶剂， 反应 31.5h， 生成 (2S,5S,3E)-2,5-bis[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-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

• Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors
  作者：Mukund K. Gurjar、Shashwati Pal、A.V. Rama Rao、Richard J. Pariza、Mukund S. Chorghade

  DOI：10.1016/s0040-4020(97)00160-9

  日期：1997.3

  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.