3',5'-di-O-acetyl-2'-S-(4-methoxyphenyl)-2'-thiouridine | 139705-84-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-di-O-acetyl-2'-S-(4-methoxyphenyl)-2'-thiouridine
• 英文别名: [(2R,3R,4R,5R)-3-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-(4-methoxyphenyl)sulfanyloxolan-2-yl]methyl acetate
• CAS: 139705-84-3
• 化学式: C₂₀H₂₂N₂O₈S
• 分子量: 450.469
• InChiKey: OKMVLTRUULPVER-NXWXRZEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-2'-S-(4-methoxyphenyl)-2'-thiouridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3',5'-di-O-acetyl-2'-deoxy-2'-<(4-methoxyphenyl)sulfonyl>uridine
  参考文献：
  名称：

  Nucleic acid related compounds. 73. Fluorination of uridine 2'-thioethers with xenon difluoride or (diethylamino)sulfur trifluoride. Synthesis of stable 2'-[alkyl(or aryl)sulfonyl]-2'-deoxy-2'-fluorouridines

  摘要：

  Treatment of 2,2'-anhydro-1-beta-D-arabinofuranosyluracil with thiolate anions gave the 2'-S-alkyl(and aryl)-2'-thiouridines (1). Oxidation of 3',5'-di-O-acetyl-2'-S-alkyl(and aryl)-2'-thiouridines (2) with 3-chloroperoxybenzoic acid (MCPBA) gave the diastereomeric sulfoxides 4. Treatment of 2 with XeF2 or 4 with (diethylamino)sulfur trifluoride/SbCl3 gave the diastereomeric 3',5'-di-O-acetyl-2'-S-alkyl(and aryl)-2'-fluoro-2'-thiouridines (9). These alpha-fluoro thioethers were oxidized (MCPBA) to their stable sulfone derivatives 11 that are analogues of the biologically active 2'-deoxy-2',2'-difluoro nucleosides. Stereochemistry (2'S) and conformations of the major diastereomers were established by X-ray crystallography. Efficient conversions of 11 to the cytidine alpha-fluoro sulfones 14 were achieved.

  DOI：

  10.1021/jo00034a031
• 作为产物：
  描述：

  2,2'-脱水尿苷 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 24.0h， 生成 3',5'-di-O-acetyl-2'-S-(4-methoxyphenyl)-2'-thiouridine
  参考文献：
  名称：

  Nucleic acid related compounds. 73. Fluorination of uridine 2'-thioethers with xenon difluoride or (diethylamino)sulfur trifluoride. Synthesis of stable 2'-[alkyl(or aryl)sulfonyl]-2'-deoxy-2'-fluorouridines

  摘要：

  Treatment of 2,2'-anhydro-1-beta-D-arabinofuranosyluracil with thiolate anions gave the 2'-S-alkyl(and aryl)-2'-thiouridines (1). Oxidation of 3',5'-di-O-acetyl-2'-S-alkyl(and aryl)-2'-thiouridines (2) with 3-chloroperoxybenzoic acid (MCPBA) gave the diastereomeric sulfoxides 4. Treatment of 2 with XeF2 or 4 with (diethylamino)sulfur trifluoride/SbCl3 gave the diastereomeric 3',5'-di-O-acetyl-2'-S-alkyl(and aryl)-2'-fluoro-2'-thiouridines (9). These alpha-fluoro thioethers were oxidized (MCPBA) to their stable sulfone derivatives 11 that are analogues of the biologically active 2'-deoxy-2',2'-difluoro nucleosides. Stereochemistry (2'S) and conformations of the major diastereomers were established by X-ray crystallography. Efficient conversions of 11 to the cytidine alpha-fluoro sulfones 14 were achieved.

  DOI：

  10.1021/jo00034a031

文献信息

• Fluorination at C2′, C3′ and C5′ of Nucleosides with 1-Chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(Tetrafluoroborate) Selectfluor^TMReagent
  作者：G. Sankar Lal

  DOI：10.1080/00397919508011410

  日期：1995.3

  Electrophilic fluorination of thioaryl ethers on the sugar component of nucleosides with commercially available SELECTFLUOR(TM) reagent provides a new method for the synthesis of C2', C3' and C5' fluoronucleosides.