(3aR,6R,6aR)-6-((tert-butyldimethylsilyloxy)methyl)-2,2,4-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol | 115130-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6R,6aR)-6-((tert-butyldimethylsilyloxy)methyl)-2,2,4-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• 英文别名: 6-O-tert-butyldimethylsilyl-3,4-isopropylidene-1-deoxy-D-psicofuranose
• CAS: 115130-14-8
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: RCTCPIJMFRZXBZ-RTWAVKEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aR)-6-((tert-butyldimethylsilyloxy)methyl)-2,2,4-trimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol 、 N6-苯甲酰基腺嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以25%的产率得到N6-benzoyl-9H-(6-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-1-deoxy-β-D-psicofuranosyl)purine
  参考文献：
  名称：

  Enhanced activity or resistance of adenosine derivatives towards adenosine deaminase-catalyzed deamination: Influence of ribose modifications

  摘要：

  The effect of the presence of the 1'-C-methyl group and 2',3'-O-substitution in the adenosine structure on ADA activity has been investigated by modeling studies. Results show that the 2'- and 3'-O-substituents are harbored in a quite large cavity of intermediate polarity, whereas the 1'-C-substituent clashes against Ala180 distorting the architecture of the catalytic centre. Globally, the study emphasizes the ability of ADA to transform a large set of 2',3'-O-substituted adenosine analogues as well as the opportunity to design 1'-C-substituted adenosine derivatives resistant to ADA-catalyzed deamination. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.084