3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione | 1021424-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione
• CAS: 1021424-65-6
• 化学式: C₂₆H₂₄N₄O₁₀
• 分子量: 552.497
• InChiKey: WRNOWGZAJZDYBN-AVKISOQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  40.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  178.0
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以97%的产率得到3-(β-D-ribofuranosyl)-5-phenyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione
  参考文献：
  名称：

  Azines and azoles: CXXVII. Glycosylation of 5,7-dihydro-4H-pyrano-[2,3-d:6,5-d′]dipyrimidine-4,6(3H)-dione and its 5-phenyl-substituted analog

  摘要：

  Glycosylation of 5-phenylpyrano[2,3-d:6,5-d']dipyrimidine-4,6-diones through the corresponding di-O-trimethylsilyl derivative with excess 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose gives a mixture of 3-mono-and 3,7-bis(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-5-phenylpyrano[2,3-d:6,5-d]dipyrimidines; in the reaction with equimolar amounts of the reactants, only the monoriboside is formed. Isomeric N,N'-disubstituted pyranodipyrimidines, as well as mixtures of their mono- and disubstituted derivatives can be separated by fractional crystallization. The alkylation of pyrano[2,3-d: 6,5-d'] dipyrimidine-4,6-di one and its 5-phenyl-substituted derivative with 2-oxabutane-1,4-diyl diacetate provides an efficient procedure for the synthesis of acyclic analogs of glycosides based on pyrano[2,3-d:6,5-d']dipyrimidines.

  DOI：

  10.1134/s1070363207040159
• 作为产物：
  描述：

  1,8-dihydroxy-9-phenyl-9H-2,4,5,7-tetraazaxanthene 在 硫酸氢铵 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 15.25h， 生成 3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione
  参考文献：
  名称：

  Azines and azoles: CXXVII. Glycosylation of 5,7-dihydro-4H-pyrano-[2,3-d:6,5-d′]dipyrimidine-4,6(3H)-dione and its 5-phenyl-substituted analog

  摘要：

  Glycosylation of 5-phenylpyrano[2,3-d:6,5-d']dipyrimidine-4,6-diones through the corresponding di-O-trimethylsilyl derivative with excess 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose gives a mixture of 3-mono-and 3,7-bis(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-5-phenylpyrano[2,3-d:6,5-d]dipyrimidines; in the reaction with equimolar amounts of the reactants, only the monoriboside is formed. Isomeric N,N'-disubstituted pyranodipyrimidines, as well as mixtures of their mono- and disubstituted derivatives can be separated by fractional crystallization. The alkylation of pyrano[2,3-d: 6,5-d'] dipyrimidine-4,6-di one and its 5-phenyl-substituted derivative with 2-oxabutane-1,4-diyl diacetate provides an efficient procedure for the synthesis of acyclic analogs of glycosides based on pyrano[2,3-d:6,5-d']dipyrimidines.

  DOI：

  10.1134/s1070363207040159