1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-β-D-gluco-pyranosyl)-uracil | 160204-60-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-β-D-gluco-pyranosyl)-uracil
• 英文别名: [(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(2,4-dioxopyrimidin-1-yl)-5-phenylselanyloxan-2-yl]methyl acetate
• CAS: 160204-60-4
• 化学式: C₂₂H₂₄N₂O₉Se
• 分子量: 539.401
• InChiKey: BGPJGMBQXXEWQQ-QNDFHXLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-β-D-gluco-pyranosyl)-uracil 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以80%的产率得到1-(2'-deoxy-3',4',6'-tri-O-acetyl-β-D-arabino-hexo-pyranosyl)-uracil
  参考文献：
  名称：

  Synthesis of 2′-deoxy-pyranosyl nucleosides from glycals through consecutive addition of phenylselenenyl chloride and glycosylation. A study of factors controlling the stereoselectivity

  摘要：

  2'-Deoxy-2'-phenylselenenyl-pyranosyl nucleosides have been synthesised in a stereoselective way starting from glycals using selenium reagents, and converted into 2'-deoxynucleosides by treatment with tributyltin hydride. The stereoselectivity of the reaction has been shown to be dependent on the protecting groups, the structure of the starting glycal, the phenylselenenyl reagent and the solvent. Nucleosides of beta-gluco beta-galacto and alpha-arabino configuration are principally obtained, starting from the corresponding benzyl protected glycals, using PhSeCl as an activating reagent and ehter as the solvent.

  DOI：

  10.1016/s0040-4020(01)89572-7
• 作为产物：
  描述：

  苯基氯化硒 、 乙酰化葡萄烯糖 在 silver trifluoromethanesulfonate 、 1,3-bis(trimethylsilyl)uracil 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-β-D-gluco-pyranosyl)-uracil 、 1-(2'-deoxy-2'-phenylselenenyl-3',4',6'-tri-O-acetyl-α-D-manno-pyranosyl)-uracil 、 1-(4',6'-O-diacetyl-2',3'-dideoxy-β-D-erythro-hex-2-enopyranosyl)uracil
  参考文献：
  名称：

  Synthesis of 2′-deoxy-pyranosyl nucleosides from glycals through consecutive addition of phenylselenenyl chloride and glycosylation. A study of factors controlling the stereoselectivity

  摘要：

  2'-Deoxy-2'-phenylselenenyl-pyranosyl nucleosides have been synthesised in a stereoselective way starting from glycals using selenium reagents, and converted into 2'-deoxynucleosides by treatment with tributyltin hydride. The stereoselectivity of the reaction has been shown to be dependent on the protecting groups, the structure of the starting glycal, the phenylselenenyl reagent and the solvent. Nucleosides of beta-gluco beta-galacto and alpha-arabino configuration are principally obtained, starting from the corresponding benzyl protected glycals, using PhSeCl as an activating reagent and ehter as the solvent.

  DOI：

  10.1016/s0040-4020(01)89572-7