2',3'-di-O-acetyl-5'-deoxy-5'(R)-fluoro-<(4-methoxyphenyl)sulfonyl>uridine | 136721-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3'-di-O-acetyl-5'-deoxy-5'(R)-fluoro-<(4-methoxyphenyl)sulfonyl>uridine
• CAS: 136721-90-9
• 化学式: C₂₀H₂₁FN₂O₁₀S
• 分子量: 500.459
• InChiKey: FQDAXECQPSCVRW-RHQZKXFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  160.06
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-acetyl-5'-deoxy-5'(R)-fluoro-<(4-methoxyphenyl)sulfonyl>uridine 在 氨 作用下， 以 甲醇 为溶剂， 以90%的产率得到5'-deoxy-5'(R)-fluoro-<(4-methoxyphenyl)sulfonyl>uridine
  参考文献：
  名称：

  Nucleic acid-related compounds. 68. Fluorination at C5' of nucleoside 5'-thioethers with DAST/antimony(III) chloride or xenon difluoride to give 5'-S-aryl-5'-fluoro-5'-thiouridines

  摘要：

  Oxidation of 2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thiouridine (2a) with 3-chloroperoxybenzoic acid (MCPBA) gave the diastereomeric sulfoxides 4a. Treatment of 2a with xenon difluoride or 4a with (diethylamino)sulfur trifluoride/antimony(III) chloride gave efficient conversions to the 2',3'-di-O-acetyl-5'-fluoro-5'-S-(4-methoxyphenyl)-5'-thiouridine diastereomers 6a. The stereochemistry and conformation of 6a(5'R) were established by X-ray crystallography. The alpha-fluoro thioethers were oxidized to their sulfoxide and sulfone derivatives with MCPBA, deprotected, and characterized.

  DOI：

  10.1021/jo00024a033
• 作为产物：
  描述：

  2',3'di-O-acetyl-5'-fluoro-5'-S-(4-methoxyphenyl)-5'-thiouridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以81%的产率得到2',3'-di-O-acetyl-5'-deoxy-5'(R)-fluoro-<(4-methoxyphenyl)sulfonyl>uridine
  参考文献：
  名称：

  Nucleic acid-related compounds. 68. Fluorination at C5' of nucleoside 5'-thioethers with DAST/antimony(III) chloride or xenon difluoride to give 5'-S-aryl-5'-fluoro-5'-thiouridines

  摘要：

  Oxidation of 2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thiouridine (2a) with 3-chloroperoxybenzoic acid (MCPBA) gave the diastereomeric sulfoxides 4a. Treatment of 2a with xenon difluoride or 4a with (diethylamino)sulfur trifluoride/antimony(III) chloride gave efficient conversions to the 2',3'-di-O-acetyl-5'-fluoro-5'-S-(4-methoxyphenyl)-5'-thiouridine diastereomers 6a. The stereochemistry and conformation of 6a(5'R) were established by X-ray crystallography. The alpha-fluoro thioethers were oxidized to their sulfoxide and sulfone derivatives with MCPBA, deprotected, and characterized.

  DOI：

  10.1021/jo00024a033