1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil | 162611-26-9

• 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-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil
• 英文别名: 1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribofuranosyl]-uracil；1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-ethynyl-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 162611-26-9
• 化学式: C₂₃H₄₀N₂O₆Si₂
• 分子量: 496.751
• InChiKey: SRDDSLJKLLGASJ-YCMMZOLNSA-N

物化性质

• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil 在 tris(dibenzylideneacetone)dipalladium (0) 1,2,2,6,6-五甲基哌啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 氟化铵 、 silver nitrate 、 lithium iodide 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 49.0h， 生成 3',3'-butadiynediyl-[(β-D-ribofuranosyl)-uracil-(β-D-ribofuranosyl)-adenine]
  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-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-[(trimethylsilyl)-ethynyl]-β-D-ribo-pentofuranosyl]uracil 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以92%的产率得到1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil
  参考文献：
  名称：

  通过向3'-β-乙炔基尿苷自由基加成苯乙烯基或巯基进行环化。3'-β-乙炔基是否是核糖核苷酸还原酶中的自旋陷阱？

  摘要：

  原位生成的苯乙烯基或噻吩基与AIBN在（2'-5'-二-O-叔丁基二甲基甲硅烷基-3'-C-乙炔基-β-D-呋喃呋喃糖基）尿嘧啶（2）上的反应得到60％和17％的收率分别环化了加合物3和4，其中通过向三键上加成苯乙烯基或噻吩基而形成的乙烯基与碱反应。3'-β-乙炔基尿苷二磷酸酯和三磷酸酯可能是核糖核苷酸还原酶瞬时巯基自由基的自旋阱。

  DOI：

  10.1016/s0040-4039(97)01308-7

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。
• 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)).