1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide | 1321592-00-0

• 英文名称: 1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide
• CAS: 1321592-00-0
• 化学式: C₁₈H₂₁N₄O₈P
• 分子量: 452.361
• InChiKey: YZDIUAGPCNWRCH-BKOGBDERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146.25
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide 在 水 、 三氟乙酸 作用下， 反应 1.0h， 以85%的产率得到1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide
  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：

  在 叔丁基过氧化氢 作用下， 以 癸烷 、 乙腈 为溶剂， 反应 0.5h， 以0.136 g的产率得到1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide
  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