5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carbonitrile | 1321591-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carbonitrile
• CAS: 1321591-89-2
• 化学式: C₁₄H₁₅IN₄O₇
• 分子量: 478.2
• InChiKey: KUYXMXXXOGEIDK-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  142.63
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-v-triazole 在 二碘甲烷 、 亚硝酸异戊酯 作用下， 反应 1.0h， 以46%的产率得到5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carbonitrile
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050