phenyl 2-deoxy-5-O-(2,6-dimethoxypyrimidin-4-yl)-3-O-methyl-1-thio-α,β-D-erythro-pentofuranoside | 259142-65-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 2-deoxy-5-O-(2,6-dimethoxypyrimidin-4-yl)-3-O-methyl-1-thio-α,β-D-erythro-pentofuranoside
• 英文别名: 2,4-dimethoxy-6-[[(2R,3S)-3-methoxy-5-phenylsulfanyloxolan-2-yl]methoxy]pyrimidine
• CAS: 259142-65-9
• 化学式: C₁₈H₂₂N₂O₅S
• 分子量: 378.449
• InChiKey: WWNBSAGYKVGPIK-RFOFMGPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2-deoxy-5-O-(2,6-dimethoxypyrimidin-4-yl)-3-O-methyl-1-thio-α,β-D-erythro-pentofuranoside 在 sodium hydroxide 、 Me₂(SMe)SBF₄ 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 73.67h， 生成 2'-deoxy-4-methoxy-3-O-methyl-2,6-dioxouridine
  参考文献：
  名称：

  Intramolecular Glycosylation to Form 4-Methoxy-2,6-Dioxopyrimidine Nucleosides via O⁶,5′-Cyclonucleosides

  摘要：

  Lewis-acid promoted intramolecular N1 glycosylation to form the novel O-6,5'-cyclonucleoside 1a occurs in high yield from the corresponding acyclic thiophenyl-glycoside 12. The relative stability of the O-6,5' tether compared with O-2,5' and O-2,3' tethers is reported. Cleavage of the anhydro bond was effected with aqueous base to yield the 4-methoxybarbituric acid nucleoside analogue 14.

  DOI：

  10.1080/07328319908044616
• 作为产物：
  描述：

  2-deoxy-5-O-(2,6-dimethoxypyrimidin-4-yl)-3-O-methyl-D-erythropentose diphenyl dithioacetal 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 以0.34 g的产率得到phenyl 2-deoxy-5-O-(2,6-dimethoxypyrimidin-4-yl)-3-O-methyl-1-thio-α,β-D-erythro-pentofuranoside
  参考文献：
  名称：

  Intramolecular Glycosylation to Form 4-Methoxy-2,6-Dioxopyrimidine Nucleosides via O⁶,5′-Cyclonucleosides

  摘要：

  Lewis-acid promoted intramolecular N1 glycosylation to form the novel O-6,5'-cyclonucleoside 1a occurs in high yield from the corresponding acyclic thiophenyl-glycoside 12. The relative stability of the O-6,5' tether compared with O-2,5' and O-2,3' tethers is reported. Cleavage of the anhydro bond was effected with aqueous base to yield the 4-methoxybarbituric acid nucleoside analogue 14.

  DOI：

  10.1080/07328319908044616