(4S,5S)-4-(4-Benzyloxy-benzyl)-5-((1R,2S)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 126410-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,5S)-4-(4-Benzyloxy-benzyl)-5-((1R,2S)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,5S)-5-[(1R,2S)-2-(hydroxymethyl)cyclopentyl]-2,2-dimethyl-4-[(4-phenylmethoxyphenyl)methyl]-1,3-oxazolidine-3-carboxylate
• CAS: 126410-90-0
• 化学式: C₃₀H₄₁NO₅
• 分子量: 495.659
• InChiKey: SEVJAVRXQUUDKH-ZDEZRRDYSA-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：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(4-Benzyloxy-benzyl)-5-((1R,2S)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 生成 (4S,5S)-4-(4-Benzyloxy-benzyl)-5-((1R,2R)-2-carboxy-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of the hydroxyethylene isostere of the HIV protease (Tyr-Pro) cleavage site

  摘要：

  The stereoselective syntheses and IC50's of Tyr-HE-Pro based inhibitors are reported. The [2S,3S,4S,5S]-stereochemistry was preferred by HIV-1 protease.

  DOI：

  10.1016/s0040-4039(00)79571-2
• 作为产物：
  描述：

  [(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester 、 2,2-二甲氧基丙烷 生成 (4S,5R)-4-(4-Benzyloxy-benzyl)-5-((1S,2R)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 、 (4S,5S)-4-(4-Benzyloxy-benzyl)-5-((1R,2S)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of the hydroxyethylene isostere of the HIV protease (Tyr-Pro) cleavage site

  摘要：

  The stereoselective syntheses and IC50's of Tyr-HE-Pro based inhibitors are reported. The [2S,3S,4S,5S]-stereochemistry was preferred by HIV-1 protease.

  DOI：

  10.1016/s0040-4039(00)79571-2

文献信息

• HIV protease inhibitors useful for the treatment of aids
  申请人：MERCK & CO. INC.

  公开号：EP0337714A2

  公开（公告）日：1989-10-18

  Compounds of the form wherein A is an amine protecting group commonly employed in peptide synthesis, G a dipeptide isostere, B an amino acid or analog thereof, and J a small terminal group are described. These compounds are useful in the inhibition of HIV protease, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.

  描述了以下形式的化合物 其中 A 是肽合成中常用的胺保护基团，G 是二肽异构体，B 是氨基酸或其类似物，J 是小末端基团。这些化合物作为化合物、药学上可接受的盐、药物组合成分，无论是否与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用，都可用于抑制 HIV 蛋白酶、预防或治疗 HIV 感染以及治疗 AIDS。还描述了治疗艾滋病的方法和预防或治疗艾滋病毒感染的方法。