2-(2,3-O-isopropylidene-β-D-ribofuranosyl)-3-methoxycarbonyl-7,7-dimethyl-4H,7H-pyrazolo[1,5-c]pyrimidine5(6H)-one | 259190-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3-O-isopropylidene-β-D-ribofuranosyl)-3-methoxycarbonyl-7,7-dimethyl-4H,7H-pyrazolo[1,5-c]pyrimidine5(6H)-one
• 英文别名: methyl 2-[(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-7,7-dimethyl-5-oxo-4,6-dihydropyrazolo[1,5-c]pyrimidine-3-carboxylate
• CAS: 259190-96-0
• 化学式: C₁₈H₂₅N₃O₇
• 分子量: 395.412
• InChiKey: MIQWMCKYTHAHIZ-ZAOWEBSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2,3-O-isopropylidene-β-D-ribofuranosyl)-3-methoxycarbonyl-7,7-dimethyl-4H,7H-pyrazolo[1,5-c]pyrimidine5(6H)-one 在 溶剂黄146 作用下， 反应 72.0h， 以84%的产率得到3-methoxycarbonyl-7,7-dimethyl-2-(β-D-ribofuranosyl)-4H,7H-pyrazolo[1,5-c]pyrimidine5(6H)-one
  参考文献：
  名称：

  Synthesis of a Novel Pyrazolo[1, 5-C]Pyrimidine C-Nucleoside and Conformational Analysis By NMR Spectroscopy

  摘要：

  Isopropylidenation of [4-methoxycarbonyl-5-(beta-D-ribofuranosyl)-1H-pyrazol-3 -yl]acetamide (1a) followed by the acidic cleavage of the sugar acetonide afforded 3-methoxycarbonyl-7, 7-dimethyl-2-(beta-D-ribofuranosyl)-4H,7H-pyrazolo[1,5-c] pyrimidine-5(6H)-one (2b), the structure of which was established unequivocally by Xray structure analysis of the monocrystals. Compounds 1a and 2b have 75% and 70% preference for the N-type puckering between C3'-endo and C3'-endo-C4'-exo forms, and a great preference of 69% and 74% for gamma(+) rotamers in solution, respectively.

  DOI：

  10.1080/07328319908044629
• 作为产物：
  描述：

  丙酮 、 [4-methoxycarbonyl-5-(β-D-ribofuranosyl)-1H-pyrazol-3-yl]acetamide 在 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以95%的产率得到2-(2,3-O-isopropylidene-β-D-ribofuranosyl)-3-methoxycarbonyl-7,7-dimethyl-4H,7H-pyrazolo[1,5-c]pyrimidine5(6H)-one
  参考文献：
  名称：

  Synthesis of a Novel Pyrazolo[1, 5-C]Pyrimidine C-Nucleoside and Conformational Analysis By NMR Spectroscopy

  摘要：

  Isopropylidenation of [4-methoxycarbonyl-5-(beta-D-ribofuranosyl)-1H-pyrazol-3 -yl]acetamide (1a) followed by the acidic cleavage of the sugar acetonide afforded 3-methoxycarbonyl-7, 7-dimethyl-2-(beta-D-ribofuranosyl)-4H,7H-pyrazolo[1,5-c] pyrimidine-5(6H)-one (2b), the structure of which was established unequivocally by Xray structure analysis of the monocrystals. Compounds 1a and 2b have 75% and 70% preference for the N-type puckering between C3'-endo and C3'-endo-C4'-exo forms, and a great preference of 69% and 74% for gamma(+) rotamers in solution, respectively.

  DOI：

  10.1080/07328319908044629