2',3'di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thiouridine | 136721-72-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2',3'di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thiouridine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-[(4-methoxyphenyl)sulfanylmethyl]oxolan-3-yl] acetate
• CAS: 136721-72-7
• 化学式: C₂₀H₂₂N₂O₈S
• 分子量: 450.469
• InChiKey: QYIYGFGWBLDBPD-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：

  2',3'di-O-acetyl-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， 以99%的产率得到2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)thiouridine sulfoxides
  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：

  乙酸酐 、 5'-S-(4-methoxyphenyl)-5'-thiouridine 在 4-二甲氨基吡啶 作用下， 反应 10.0h， 以99%的产率得到2',3'di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thiouridine
  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

文献信息

• Robins, Morris J.; Wnuk, Stanislaw F., Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 71 - 88
  作者：Robins, Morris J.、Wnuk, Stanislaw F.

  DOI：——

  日期：——
• 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
  作者：Morris J. Robins、Stanislaw F. Wnuk、Khairuzzaman B. Mullah、N. Kent Dalley

  DOI：10.1021/jo00024a033

  日期：1991.11

  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.