phosphoric acid mono-[(2R,3S,5R)-3,4-dihydroxy-5-(4-piperidin-2-yl-[1,2,3]triazol-1-yl)-tetrahydro-furan-2-ylmethyl] ester | 1185506-07-3

• 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: phosphoric acid mono-[(2R,3S,5R)-3,4-dihydroxy-5-(4-piperidin-2-yl-[1,2,3]triazol-1-yl)-tetrahydro-furan-2-ylmethyl] ester
• 英文别名: [(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-piperidin-2-yltriazol-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 1185506-07-3
• 化学式: C₁₂H₂₁N₄O₇P
• 分子量: 364.295
• InChiKey: YJUNMIQIOBUCCV-KVQAKGFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  159
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  phosphoric acid (3aR,4R,6R)-2,2-dimethyl-6-(4-piperidin-2-yl-[1,2,3]triazol-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester diethyl ester 在 三甲基溴硅烷 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 phosphoric acid mono-[(2R,3S,5R)-3,4-dihydroxy-5-(4-piperidin-2-yl-[1,2,3]triazol-1-yl)-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  β-1,2,3-Triazolyl-Nucleosides as Nicotinamide Riboside Mimics

  摘要：

  The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogenation conditions. These analogues were modelled as to define their similarity to nicotinamide riboside and quantify their ability to bind NAD-dependent protein deacetylases.

  DOI：

  10.1080/15257770902865415

文献信息

• β-1,2,3-Triazolyl-Nucleosides as Nicotinamide Riboside Mimics
  作者：E. J. Amigues、E. Armstrong、M. Dvorakova、M. E. Migaud、M. Huang

  DOI：10.1080/15257770902865415

  日期：2009.4.28

  The synthesis of a series of pyridine- and piperidine-substituted 1,2,3-triazolides linked to a riboside moiety is described. The presence of a triazolide substituent on the pyridine moiety permitted the facile reduction of the latter under mild hydrogenation conditions. These analogues were modelled as to define their similarity to nicotinamide riboside and quantify their ability to bind NAD-dependent protein deacetylases.