1-(2',3',5'-tri-O-Benzoyl-D-ribofuranosyl)-5,6,7,8-tetrahydro-3-phenylbenzothieno<2,3-d>pyrimidin-2,4(1H,3H)-dion | 155199-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2',3',5'-tri-O-Benzoyl-D-ribofuranosyl)-5,6,7,8-tetrahydro-3-phenylbenzothieno<2,3-d>pyrimidin-2,4(1H,3H)-dion
• CAS: 155199-71-6
• 化学式: C₄₂H₃₄N₂O₉S
• 分子量: 742.806
• InChiKey: CGGUJOATQUSADE-QXOYWFLQSA-N

物化性质

• 沸点：
  877.2±75.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  54.0
• 可旋转键数：
  9.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  132.13
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-(2',3',5'-tri-O-Benzoyl-D-ribofuranosyl)-5,6,7,8-tetrahydro-3-phenylbenzothieno<2,3-d>pyrimidin-2,4(1H,3H)-dion 在 甲醇 、 氨 作用下， 反应 72.0h， 以80%的产率得到1-D-Ribofuranosyl-5,6,7,8-tetrahydro-3-phenylbenzothieno<2,3-d>pyrimidin-2,4(1H,3H)-dion
  参考文献：
  名称：

  Heterocyclische ?-Enaminoester. 57. Studien zur N-Glycosidierung heterokondensierter Uracile

  摘要：

  N-Glycosylations of various heterocondensed uracils of the general type 4 are described. The thieno[2,3-d]pyrimidines (9a-e) afford with 1-0-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (7) the corresponding 1-ribosides (10a-e) in a modified Hilbert-Johnson-Birkofer synthesis; from these 10a was smoothly saponified to give the free riboside 11a. - In a more generally applicable stereospecific sodium salt glycosylation procedure employing alpha-acetobromglucose, the 1-glucosides 12-16 and with beta-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) a variation of acyclonucleosides 17-22 have been obtained. The structure of 18a has been confirmed by X-ray analysis.

  DOI：

  10.1002/prac.19943360206
• 作为产物：
  描述：

  3-phenyl-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidine-2,4-dione 在 aluminum(III) sulfate 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 1-(2',3',5'-tri-O-Benzoyl-D-ribofuranosyl)-5,6,7,8-tetrahydro-3-phenylbenzothieno<2,3-d>pyrimidin-2,4(1H,3H)-dion
  参考文献：
  名称：

  Heterocyclische ?-Enaminoester. 57. Studien zur N-Glycosidierung heterokondensierter Uracile

  摘要：

  N-Glycosylations of various heterocondensed uracils of the general type 4 are described. The thieno[2,3-d]pyrimidines (9a-e) afford with 1-0-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (7) the corresponding 1-ribosides (10a-e) in a modified Hilbert-Johnson-Birkofer synthesis; from these 10a was smoothly saponified to give the free riboside 11a. - In a more generally applicable stereospecific sodium salt glycosylation procedure employing alpha-acetobromglucose, the 1-glucosides 12-16 and with beta-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) a variation of acyclonucleosides 17-22 have been obtained. The structure of 18a has been confirmed by X-ray analysis.

  DOI：

  10.1002/prac.19943360206