6-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6H-[1,2,4]triazolo[1,5-c]pyrimidin-5-one | 138840-88-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 6-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6H-[1,2,4]triazolo[1,5-c]pyrimidin-5-one
• CAS: 138840-88-7
• 化学式: C₁₆H₂₆N₄O₅Si
• 分子量: 382.492
• InChiKey: AMGSRUIAGARZIW-FMKGYKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  111.11
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6H-[1,2,4]triazolo[1,5-c]pyrimidin-5-one 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.83h， 生成 6-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-6H-[1,2,4]triazolo[1,5-c]pyrimidin-5-one
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 4-二甲氨基吡啶 、 bis(trimethylsilyl)trifluoroacetamide 、 三氟甲磺酸三甲基硅酯 、 氨 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 6-[(2R,3R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-6H-[1,2,4]triazolo[1,5-c]pyrimidin-5-one
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7