(2RS,5S)-N-{9-[5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide | 1024613-24-8

• 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: (2RS,5S)-N-{9-[5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide
• CAS: 1024613-24-8
• 化学式: C₃₀H₃₇N₅O₃Si
• 分子量: 543.741
• InChiKey: KXVRMCQEYFNDRA-FZNWDQQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2RS,5S)-N-{9-[5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide 在 四丁基氟化铵 作用下， 反应 2.0h， 以100%的产率得到(2RS,5S)-N-{9-[5-benzyl-5-(hydroxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide
  参考文献：
  名称：

  Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

  摘要：

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.028
• 作为产物：
  描述：

  (5S)-5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-ol 、 N6-苯甲酰基腺嘌呤 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以55%的产率得到(2RS,5S)-N-{9-[5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-9H-purin-6-yl}benzamide
  参考文献：
  名称：

  Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

  摘要：

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.028