Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside | 166320-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside
• 英文别名: (3aR,6R,7aS)-6-methoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-thione
• CAS: 166320-79-2
• 化学式: C₇H₁₀O₄S
• 分子量: 190.22
• InChiKey: LOUCKVVJLVPHFM-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside 在 ammonium hydroxide 、 四丁基溴化铵 作用下， 生成 Methyl 3-O-carbamoyl-2-deoxy-4-thio-β-D-ribopyranoside 、 Methyl 4-O-carbamoyl-2-deoxy-3-thio-β-D-ribopyranoside
  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
• 作为产物：
  描述：

  甲醇 、 2-deoxy-D-ribose 、 N,N'-硫羰基二咪唑 在 盐酸 作用下， 生成 Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside
  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

文献信息

• 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
  作者：Karamjit Singh Jandu、David L. Selwood

  DOI：10.1021/jo00121a039

  日期：1995.8

  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.