(1'S,4''R)-9-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-6-chloro-9H-purine | 688311-37-7

• 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: (1'S,4''R)-9-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-6-chloro-9H-purine
• 英文别名: tert-butyl-[(S)-(6-chloropurin-9-yl)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-dimethylsilane
• CAS: 688311-37-7
• 化学式: C₁₇H₂₇ClN₄O₃Si
• 分子量: 398.965
• InChiKey: WQKLEIIDVYWVBI-ABAIWWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1'S,4''R)-9-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-6-chloro-9H-purine 在 溶剂黄146 作用下， 反应 24.0h， 以68%的产率得到(2R,3S)-3-(tert-butyldimethylsilanyloxy)-3-(6-chloro-purin-9-yl)propane-1,2-diol
  参考文献：
  名称：

  Silylative N-hydroxyalkylation of amide compounds: application to the synthesis of acyclic alditol-based nucleoside analogues

  摘要：

  A rare silylative hydroxyalkylation of amide compounds with chiral aldehydes has been developed utilizing a Lewis acid-Lewis base promoter system consisting of an equimolecular mixture of tert-butyldimethylsilyl trifluoromethanesulfonate and N-diisopropylethylamine. This approach culminated in the synthesis of several enantiopure acyclic nucleoside representatives comprising thymidine analogues 6, 7, 9, 10, 12 and 13, uridine analogues 15 and 16, and 6-chloropurine derivatives 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.008
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 6-氯嘌呤 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.17h， 以55%的产率得到(1'R,4''R)-9-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-6-chloro-9H-purine
  参考文献：
  名称：

  Silylative N-hydroxyalkylation of amide compounds: application to the synthesis of acyclic alditol-based nucleoside analogues

  摘要：

  A rare silylative hydroxyalkylation of amide compounds with chiral aldehydes has been developed utilizing a Lewis acid-Lewis base promoter system consisting of an equimolecular mixture of tert-butyldimethylsilyl trifluoromethanesulfonate and N-diisopropylethylamine. This approach culminated in the synthesis of several enantiopure acyclic nucleoside representatives comprising thymidine analogues 6, 7, 9, 10, 12 and 13, uridine analogues 15 and 16, and 6-chloropurine derivatives 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.008

文献信息

• Silylative N-hydroxyalkylation of amide compounds: application to the synthesis of acyclic alditol-based nucleoside analogues
  作者：Lucia Battistini、Giovanni Casiraghi、Claudio Curti、Gloria Rassu、Vincenzo Zambrano、Franca Zanardi

  DOI：10.1016/j.tet.2004.02.008

  日期：2004.3

  A rare silylative hydroxyalkylation of amide compounds with chiral aldehydes has been developed utilizing a Lewis acid-Lewis base promoter system consisting of an equimolecular mixture of tert-butyldimethylsilyl trifluoromethanesulfonate and N-diisopropylethylamine. This approach culminated in the synthesis of several enantiopure acyclic nucleoside representatives comprising thymidine analogues 6, 7, 9, 10, 12 and 13, uridine analogues 15 and 16, and 6-chloropurine derivatives 18 and 19. (C) 2004 Elsevier Ltd. All rights reserved.