N¹-benzyl-2',3'-O-benzylidene guanosine | 214918-86-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N¹-benzyl-2',3'-O-benzylidene guanosine
• 英文别名: 1-benzyl-9-(2',3'-O-benzylidene-β-D-ribofuranosyl)guanine；9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-phenyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-amino-1-benzylpurin-6-one
• CAS: 214918-86-2
• 化学式: C₂₄H₂₃N₅O₅
• 分子量: 461.477
• InChiKey: NMYSEBMNWCDEOO-CDMSWCOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N¹-benzyl-2',3'-O-benzylidene guanosine 在 4-二甲氨基吡啶 作用下， 反应 24.0h， 生成 1-Benzyl-9-[(3aR,4R,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-{[1-phenyl-meth-(E)-ylidene]-amino}-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Unexpected reactivity of N2-benzylidene guanosine derivatives

  摘要：

  Guanosine derivatives masked at the sugar are protected at N-2 by a benzylideneamine group for the first time. The free 5'-hydroxyl function reveals to be incompatible with the N-2-protective group that is then rapidly hydrolyzed to regenerate the free exocyclic amine. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02074-7
• 作为产物：
  描述：

  1-Benzyl-9-[(3aR,4R,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-{[1-phenyl-meth-(E)-ylidene]-amino}-1,9-dihydro-purin-6-one 在 四丁基氟化铵 作用下， 以100%的产率得到N¹-benzyl-2',3'-O-benzylidene guanosine
  参考文献：
  名称：

  Unexpected reactivity of N2-benzylidene guanosine derivatives

  摘要：

  Guanosine derivatives masked at the sugar are protected at N-2 by a benzylideneamine group for the first time. The free 5'-hydroxyl function reveals to be incompatible with the N-2-protective group that is then rapidly hydrolyzed to regenerate the free exocyclic amine. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02074-7

文献信息

• Synthesis of Enzymatically Stable Analogues of GDP for Binding Studies with Transducin, the G-Protein of the Visual Photoreceptor
  作者：Stéphane Vincent、Sonya Grenier、Alain Valleix、Christian Salesse、Luc Lebeau、Charles Mioskowski

  DOI：10.1021/jo9806207

  日期：1998.10.1

  final deprotection step was achieved by catalytic hydrogenolysis. The biological properties of the compounds have been evaluated toward transducin, the G-protein of the visual photoreceptor. Three guanosine imidodiphosphate derivatives bearing a linker at different positions on the sugar and on the base were then prepared and evaluated, giving some insight into the GDP binding site of transducin.

  进行了五种鸟嘌呤二磷酸鸟嘌呤（GDP）的酶促稳定类似物的合成。焦磷酸部分依次被丙二酸酯，乙酰膦酸酯，膦酰基乙酸酯，亚甲基双膦酸酯和亚氨基二磷酸酯基团模拟。所有化合物都是通过合成一个瞬态完全保护的核苷二磷酸类似物来制备的，最后的脱保护步骤是通过催化氢解来实现的。已针对视觉感光器的G蛋白转导素评估了化合物的生物学特性。然后制备并评估了三种在糖上和碱基上不同位置带有连接子的鸟嘌呤亚氨基二磷酸衍生物，从而对转导蛋白的GDP结合位点有所了解。
• Unexpected reactivity of N2-benzylidene guanosine derivatives
  作者：Stéphane Mons、Luc Lebeau、Charles Mioskowski

  DOI：10.1016/s0040-4039(98)02074-7

  日期：1998.12

  Guanosine derivatives masked at the sugar are protected at N-2 by a benzylideneamine group for the first time. The free 5'-hydroxyl function reveals to be incompatible with the N-2-protective group that is then rapidly hydrolyzed to regenerate the free exocyclic amine. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.