3-deoxy-3-iodo-1,2-O-(1-methylethylidene)-α-D-ribofuranose | 532957-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-iodo-1,2-O-(1-methylethylidene)-α-D-ribofuranose
• 英文别名: [(3aR,5R,6R,6aS)-6-iodo-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• CAS: 532957-58-7
• 化学式: C₈H₁₃IO₄
• 分子量: 300.093
• InChiKey: CLHRXADGCGPDER-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-iodo-1,2-O-(1-methylethylidene)-α-D-ribofuranose 在 三乙基硼 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 41.0h， 生成 ((3aR,5S,6S,6aR)-6-Ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol
  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：

  [(3aR,5R,6R,6aS)-6-iodo-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy-tert-butyl-diphenylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到3-deoxy-3-iodo-1,2-O-(1-methylethylidene)-α-D-ribofuranose
  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