1-[2-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil | 399513-32-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[2-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil
• 英文别名: 1-[2-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribofuranosyl]-uracil；1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-ethynyl-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 399513-32-7
• 化学式: C₁₇H₂₆N₂O₆Si
• 分子量: 382.489
• InChiKey: BFPOFWCSOJEYMU-ABYLEIOUSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil 在 吡啶 、 4-二甲氨基吡啶 、 copper diacetate 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 3',3'-butadiynediyl-bis-[(3,5-di-O-acetyl-2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]
  参考文献：
  名称：

  Synthesis of Nucleoside Dimers Bridged on Ribose with a Butadiynyl Group

  摘要：

  [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.

  DOI：

  10.1021/ol026584m
• 作为产物：
  描述：

  1-[2-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)ethynyl]-β-D-ribo-pentofuranosyl]uracil 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以72%的产率得到1-[2-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil
  参考文献：
  名称：

  1-（3-C-（PROPA-1,2-二烯基）-D-RIBO-戊呋喃糖基）尿嘧啶核苷的制备

  摘要：

  Crabbé反应扩展到C-3'-烯基-尿苷的制备。研究了溶剂和保护基对反应的影响。二甲苯基中的二甲苯基在回流的二恶烷中的转化进行到相应的烯丙基核苷7; 而在回流THF中得到曼尼希碱5。测试了完全脱保护的曼尼希碱和烯丙基尿苷6和9的抗肿瘤活性。

  DOI：

  10.1081/ncn-100107189

文献信息

• PREPARATION OF 1-(3-C-(PROPA-1,2-DIENYL)-D-<i>RIBO</i>-PENTOFURANOSYL)URACIL, AN ALLENIC NUCLEOSIDE
  作者：Jérôme Dauvergne、Alain Burger、Jean-François Biellmann

  DOI：10.1081/ncn-100107189

  日期：2001.12.31

  The Crabbé reaction was extended to the preparation of C-3′-allenyl-uridine. The effects of solvent and protecting group on the reaction were studied. The conversion in refluxing dioxan of disilyl either 3 proceeds to the corresponding allenic nucleoside 7; whereas, in refluxing THF the Mannich base 5 was obtained. Fully deprotected Mannich base and allenic uridines 6 and 9 were tested for their antitumor

  Crabbé反应扩展到C-3'-烯基-尿苷的制备。研究了溶剂和保护基对反应的影响。二甲苯基中的二甲苯基在回流的二恶烷中的转化进行到相应的烯丙基核苷7; 而在回流THF中得到曼尼希碱5。测试了完全脱保护的曼尼希碱和烯丙基尿苷6和9的抗肿瘤活性。
• 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.