3'-O-carbamoyl-5-ethyl-4'-thio-2'-deoxyuridine | 166320-88-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-O-carbamoyl-5-ethyl-4'-thio-2'-deoxyuridine
• 英文别名: [(2R,3S,5S)-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)-2-(hydroxymethyl)thiolan-3-yl] carbamate
• CAS: 166320-88-3
• 化学式: C₁₂H₁₇N₃O₅S
• 分子量: 315.35
• InChiKey: LHCGVTOYWXNRQJ-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-carbamoyl-5-ethyl-4'-thio-2'-deoxyuridine 在 三乙胺 、 对甲苯磺酰氯 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 sulfone of 5'-pyridinium-3',4'-didehydro-5-ethyl-4'-thio-2'-deoxyuridine
  参考文献：
  名称：

  Some Reactions of 4′-Thionucleosides and Their Sulfones

  摘要：

  We report interesting and novel reactions of 4'-thionucleosides and their sulfone derivatives when a good leaving group is present in the 5'-position. The results have important implications for the phosphorylation of these nucleoside analogues by standard chemical procedures. Possible mechanisms for these reactions are discussed.

  DOI：

  10.1080/07328319608002376
• 作为产物：
  描述：

  Methyl 3-O-carbamoyl-2-deoxy-4-thio-β-D-ribopyranoside 在 Dowex 50W-X₈ 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 3'-O-carbamoyl-5-ethyl-4'-thio-2'-deoxyuridine
  参考文献：
  名称：

  4'-Thio-Nucleosides via in Situ Pyranose-Furanose Rearrangements: A Short Synthesis of the Antiherpes Agent 2'-Deoxy-5-ethyl-4'-thiouridine via Direct Coupling of a Silylated Pyrimidine Base with a 4-Thiopyranose Sugar

  摘要：

  Methyl 2-deoxy-3,4-0-thiocarbonyl-beta-D-ribopyranoside was converted into the thione carbonate by reaction with thiophosgene. Bromide ion-catalyzed 0-S rearrangement produced methyl 2-deoxy-3-0,4-S-carbonyl-4-thio-beta-D-ribopyranoside (3a) and the 3-0,4-S isomer 3b. The carbonates were cleaved with ammonia and the 3-0,4-S pyranoside sugar coupled with bis(trimethylsilyl)-5-ethyluracil using trimethylsilyl triflate to provide the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine 9. The reaction proceeded via in, situ pyranoside rearrangement-of the sugar and subsequent coupling. The pyranoside sugar could also be converted to the furanoside form with Dowex H+ acid resin and coupled in conventional fashion to give the nucleoside. Coupling of methyl 4-0-carbamoyl-2-deoxy-3-thio-beta-D-ribopyranoside (4b) with the bis(trimethylsilyl)-5-ethyluracil gave 1-[2-[2-(hydroxymethyl)thiiran-1-yl]-1-methoxyethyl]-5-ethyluracil.

  DOI：

  10.1021/jo00121a039