phosphoric acid (3aR,4R,6R)-2,2-dimethyl-6-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester diethyl ester | 1185506-05-1

• 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: phosphoric acid (3aR,4R,6R)-2,2-dimethyl-6-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester diethyl ester
• CAS: 1185506-05-1
• 化学式: C₁₉H₂₇N₄O₇P
• 分子量: 454.42
• InChiKey: TWTARKFIKINOCH-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  116.05
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  phosphoric acid (3aR,4R,6R)-2,2-dimethyl-6-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester diethyl ester 在 甲酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以49%的产率得到5-O-diethylphosphate-2,3-O-isopropylidene-1-N-(4'-piperidin-3''-yl)-[1',2',3']-triazole-β-D-ribofuranoside
  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
• 作为产物：
  描述：

  二乙基亚磷酰氯 、 [(3aR,4R,6R,6aR)-2,2-dimethyl-6-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]methanol 在 三乙胺 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以85%的产率得到phosphoric acid (3aR,4R,6R)-2,2-dimethyl-6-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester diethyl 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