1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide | 1321592-02-2

• 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: 1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(2-oxo-4H-1,3,2lambda5-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-2-yl]triazole-4-carboxamide；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(2-oxo-4H-1,3,2λ5-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-2-yl]triazole-4-carboxamide
• CAS: 1321592-02-2
• 化学式: C₁₅H₁₇N₄O₈P
• 分子量: 412.296
• InChiKey: CLSPMQYZFZBNFW-FTSXSUCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3-O-isopropylidene-β-D-ribofuranosyl-1-azide 在 吡啶 、 叔丁基过氧化氢 、 二(氰基苯)二氯化钯 、 二碘甲烷 、 水 、 sodium methylate 、 三乙胺 、 三氟乙酸 、 potassium hydroxide 、 亚硝酸异戊酯 作用下， 以 甲醇 、 癸烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.33h， 生成 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

文献信息

• 5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties
  作者：Tomasz Ostrowski、Piotr Januszczyk、Marcin Cieslak、Julia Kazmierczak-Baranska、Barbara Nawrot、Elzbieta Bartoszak-Adamska、Joanna Zeidler

  DOI：10.1016/j.bmc.2011.05.050

  日期：2011.7

  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.