5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide | 99249-19-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-amino-4-carbamoyltriazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 99249-19-1
• 化学式: C₁₄H₁₉N₅O₈
• 分子量: 385.334
• InChiKey: QPUNHZNHZYBWTF-IDTAVKCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  188
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide 在 吡啶 、 对甲苯磺酰氯 作用下， 反应 24.0h， 以59%的产率得到5-amino-4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuanosyl)-v-triazole
  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
• 作为产物：
  描述：

  乙酸酐 、 5-amino-1-β-D-ribofuranosyl-V-triazole-4-carboxaldehyde 在 吡啶 作用下， 反应 18.0h， 生成 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide
  参考文献：
  名称：

  Total synthesis of (4R)- and (4S)-5,6-dihydro-1-.beta.-D-ribofuranosyl-4H-pyrazolo[3,4-d][1,3]diazepin-4-ol and (8R)- and (8S)-7,8-dihydro-3-.beta.-D-ribofuranosyl-6H-v-triazolo[4,5-d][1,3]diazepin-8-ol: two heterocyclic analogs of the nucleoside antibiotic coformycin

  摘要：

  DOI：

  10.1021/jo00357a020