(2',5'-di-O-tert-butyldimethylsilyl-3'-C-ethynyl-β-D-ribo-furanosyl)adenine | 162611-25-8

• 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: (2',5'-di-O-tert-butyldimethylsilyl-3'-C-ethynyl-β-D-ribo-furanosyl)adenine
• 英文别名: 9-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribofuranosyl]adenine；(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-ethynyloxolan-3-ol
• CAS: 162611-25-8
• 化学式: C₂₄H₄₁N₅O₄Si₂
• 分子量: 519.792
• InChiKey: AFTRVHVIQSPYJH-QCHQBCSNSA-N

物化性质

• 熔点：
  225-227 °C
• 沸点：
  584.4±60.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2',5'-di-O-tert-butyldimethylsilyl-3'-C-ethynyl-β-D-ribo-furanosyl)adenine 在 Lindlar's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-vinyl-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
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 为溶剂， 生成 (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

文献信息

• Synthesis of Nucleoside Dimers Bridged on Ribose with a Butadiynyl Group
  作者：Françoise Jung、Alain Burger、Jean-François Biellmann

  DOI：10.1021/ol026584m

  日期：2003.2.1

  [GRAPHICS]The nucleoside dimer linked by a butadiynediyl group at C-3'beta may serve as a building block for the preparation of backbone-modified oligonucleotides for DNA repair or mutation in functional genomics. We prepared this type of dimer by an Eglington or Sonogashira coupling reaction. The unsymmetrical dimer was synthesized by coupling the acetylene with the bromoacetylene. Only marginal cytotoxicity was detected for one of the dimers.
• 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.
• Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides
  作者：Pierre M.J Jung、Alain Burger、Jean-Francois Biellmann

  DOI：10.1016/0040-4039(94)02434-d

  日期：1995.2

  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)).