2'-deoxy-2'-C-ethynyluridine | 517893-32-2

• 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: 2'-deoxy-2'-C-ethynyluridine
• 英文别名: 1-(2-deoxy-2-C-ethynyl-β-D-ribo-pentofuranosyl)uracil；2'-Ethynyl-2'-deoxyuridine；1-[(2R,3R,4S,5R)-3-ethynyl-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 517893-32-2
• 化学式: C₁₁H₁₂N₂O₅
• 分子量: 252.227
• InChiKey: TZVVBAOQUFXLTJ-GTDKDYCYSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-C-ethynyluridine 在 吡啶 、 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 49.0h， 生成 1-(2-deoxy-2-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine
  参考文献：
  名称：

  The First Radical Method for the Introduction of an Ethynyl Group Using a Silicon Tether and Its Application to the Synthesis of 2‘-Deoxy-2‘-C-ethynylnucleosides¹

  摘要：

  A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3B followed by tetrabutylammonium fluoride in toluene, atom transfer 5-exo-cyclization and subsequent elimination occurred to give cis-2-ethynylindanol in high yield. The method was shown to be useful in the introduction of an ethynyl group in various five- and six-membered-ring iodohydrins. Furthermore, 2'-deoxy-2'-C-ethynyl-uridine (6) and -cytidine (7), which were designed as novel antimetabolites, were readily synthesized by using this method as the key step. This would be the first example in which a radical reaction was used for introducing an ethynyl group.

  DOI：

  10.1021/jo0206667
• 作为产物：
  描述：

  1-[5-O-(4-methoxytrityl)-2-deoxy-2-iodo-3-O-(trimethylsilyl)ethynyldimethylsilyl-β-D-ribo-pentofuranosyl]uracil 在 三乙基硼 、 三氟乙酸 作用下， 以 正己烷 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 2'-deoxy-2'-C-ethynyluridine
  参考文献：
  名称：

  The First Radical Method for the Introduction of an Ethynyl Group Using a Silicon Tether and Its Application to the Synthesis of 2‘-Deoxy-2‘-C-ethynylnucleosides¹

  摘要：

  A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3B followed by tetrabutylammonium fluoride in toluene, atom transfer 5-exo-cyclization and subsequent elimination occurred to give cis-2-ethynylindanol in high yield. The method was shown to be useful in the introduction of an ethynyl group in various five- and six-membered-ring iodohydrins. Furthermore, 2'-deoxy-2'-C-ethynyl-uridine (6) and -cytidine (7), which were designed as novel antimetabolites, were readily synthesized by using this method as the key step. This would be the first example in which a radical reaction was used for introducing an ethynyl group.

  DOI：

  10.1021/jo0206667

文献信息

• A New Entry to the Stereoselective Introduction of an Ethynyl Group by a Radical Reaction: Synthesis of the Potential Antimetabolite 2′-Deoxy-2′-C-ethynyluridine
  作者：Makoto Sukeda、Satoshi Ichikawa、Akira Matsuda、Satoshi Shuto

  DOI：10.1002/anie.200290037

  日期：2002.12.16