(1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane | 175471-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane
• 英文别名: 9-[(1S,2S,4S,5R)-4-[(2-methylpropan-2-yl)oxy]-5-(phenylmethoxymethyl)-2-bicyclo[3.1.0]hexanyl]purin-6-amine
• CAS: 175471-22-4
• 化学式: C₂₃H₂₉N₅O₂
• 分子量: 407.516
• InChiKey: CPOVVEQDRTXAFJ-YDSTWLSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane 在 ammonium hydroxide 、 三氯化硼 作用下， 生成 (1R,2S,4S,5S)-1-hydroxymethyl-2-hydroxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template

  摘要：

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.

  DOI：

  10.1080/07328319608002382
• 作为产物：
  描述：

  (1S,4R,5S)-3-<(benzyloxy)methyl>-4-tert-butyloxy-5-hydroxy-2-cyclopenten-1-ol 在 ammonium hydroxide 、 三氢化钐 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium hydride 、 三苯基膦 、 mercury dichloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 88.92h， 生成 (1R,2S,4S,5S)-1-<(benzyloxy)methyl>-2-tert-butyloxy-4-(6-amino-9-purinyl)bicyclo<3.1.0>hexane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template

  摘要：

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.

  DOI：

  10.1080/07328319608002382

文献信息

• Synthesis, Conformational Analysis, and Biological Activity of a Rigid Carbocyclic Analogue of 2′-Deoxy Aristeromycin Built on a Bicyclo[3.1.0]hexane Template
  作者：Maqbool A. Siddiqui、Harry Ford、Clifford George、Victor E. Marquez

  DOI：10.1080/07328319608002382

  日期：1996.1

  A new chiral synthesis of the pseudosugar synthon (1R,2S,4R,5S)-1-[(benzyloxy)methyl]-2-tert-butyloxy-4-hydroxybicyclo[3.1.0]hexane (12) is reported. This compound was used as a template for the construction of carbocyclic nucleoside 4, a conformationally rigid analogue of 2'-deoxyaristeromycin. The X-ray structure and H-1 NMR analysis confirmed the exclusive North [2'-exo ((2)E)] conformation of 4 which is vastly different from that of other non-rigid carbocyclic nucleosides. Compound 4 showed good in vitro antiviral activity against human cytomegalovirus and EBV with minimal cytotoxicity.