1-(3,5-O-diacetyl-2-deoxy-2-C-ethynyl-β-D-ribo-pentofuranosyl)uracil | 532957-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-O-diacetyl-2-deoxy-2-C-ethynyl-β-D-ribo-pentofuranosyl)uracil
• 英文别名: [(2R,3S,4R,5R)-3-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-ethynyloxolan-2-yl]methyl acetate
• CAS: 532957-62-3
• 化学式: C₁₅H₁₆N₂O₇
• 分子量: 336.301
• InChiKey: HSOPPOLGAHRQJQ-MHDGFBEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,5-O-diacetyl-2-deoxy-2-C-ethynyl-β-D-ribo-pentofuranosyl)uracil 在 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 、 三乙胺 、 ammonium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 25.0h， 以88%的产率得到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 吡啶 、 三乙基硼 、 三氟乙酸 作用下， 以 正己烷 、 水 、 甲苯 为溶剂， 反应 31.0h， 生成 1-(3,5-O-diacetyl-2-deoxy-2-C-ethynyl-β-D-ribo-pentofuranosyl)uracil
  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