3',5'-di-O-acetyl-2'(S)-fluoro-2'-S-(4-methoxyphenyl)-2'-thiouridine | 139706-00-6

• 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)-fluoro-2'-S-(4-methoxyphenyl)-2'-thiouridine
• 英文别名: 3',5'-di-O-acetyl-2'(R)-fluoro-2'-S-(4-methoxyphenyl)-2'-thiouridine；3',5'-di-O-acetyl-2'-fluoro-2'-S-(4-methoxyphenyl)-2'-thiouridine
• CAS: 139706-00-6；139706-01-7
• 化学式: C₂₀H₂₁FN₂O₈S
• 分子量: 468.46
• InChiKey: XQZFSTCPSKEZMY-KIAIFBHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32.0
• 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：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-acetyl-2'(S)-fluoro-2'-S-(4-methoxyphenyl)-2'-thiouridine 在 氨 、 水 、 三乙胺 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 46.0h， 生成 2'-deoxy-2'(S)-fluoro-2'-<(4-methoxyphenyl)sulfonyl>cytidine
  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：

  3',5'-di-O-acetyl-2'-deoxy-2'(R-S)-<(4-methoxyphenyl)sulfinyl>uridine 在 二氟代氙 、 二乙胺基三氟化硫 、 三氯化锑 作用下， 以 二氯甲烷 为溶剂， 反应 27.5h， 生成 3',5'-di-O-acetyl-2'(S)-fluoro-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

• Bis(2-methoxyethyl)aminosulfur Trifluoride:  A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability
  作者：Gauri S. Lal、Guido P. Pez、Reno J. Pesaresi、Frank M. Prozonic、Hansong Cheng

  DOI：10.1021/jo990566+

  日期：1999.9.1

  Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)(2)NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)(2)NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.