(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-trimethylsilanylethynyl-tetrahydro-furan-3-ol | 162611-17-8

• 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: (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-trimethylsilanylethynyl-tetrahydro-furan-3-ol
• CAS: 162611-17-8
• 化学式: C₂₇H₄₉N₅O₄Si₃
• 分子量: 591.974
• InChiKey: DMDGVYJSVQDAOL-OJUMFBKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  117.54
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-trimethylsilanylethynyl-tetrahydro-furan-3-ol 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(2',5'-di-O-tert-butyldimethylsilyl-3'-C-ethynyl-β-D-ribo-furanosyl)adenine
  参考文献：
  名称：

  Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides

  摘要：

  In order to prepare new anti-retroviral nucleoside analogues, the effect of the group at C-5' on the addition of lithium and cerium trimethylsilylacetylide on 3'-ketonucleosidcs (R(1) = H, R(1) = TBDMS) derived from adenosine and uridine was studied. The best results in respect of yield (56 to 81%) and diastereoselectivity (95:5 to >98:2) were obtained with a cerium reagent (RCcCl(2)).

  DOI：

  10.1016/0040-4039(94)02434-d
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 生成 (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-trimethylsilanylethynyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides

  摘要：

  In order to prepare new anti-retroviral nucleoside analogues, the effect of the group at C-5' on the addition of lithium and cerium trimethylsilylacetylide on 3'-ketonucleosidcs (R(1) = H, R(1) = TBDMS) derived from adenosine and uridine was studied. The best results in respect of yield (56 to 81%) and diastereoselectivity (95:5 to >98:2) were obtained with a cerium reagent (RCcCl(2)).

  DOI：

  10.1016/0040-4039(94)02434-d

文献信息

• Radical cyclisation mediates the synthesis of a new base-ribose carbon bridged adenosine
  作者：Pascal Lang、Alain Mayer、Pierre Jung、Denis Tritsch、Jean-François Biellmann、Alain Burger

  DOI：10.1016/j.tetlet.2004.03.176

  日期：2004.5

  Reaction of tributylstannyl, radical generated in situ with AIBN, with (2',5'-di-O-tert-butyldimethylsilyl-3'-C-ethynyl-beta-D-ribo-furanosyl)adenine (5) gave in 690% yield the new conformationally locked nucleosides 6 (EIZ). (C) 2004 Elsevier Ltd. All rights reserved.