3'-O-acetyl-2'-O-triflyl-4,5'-anhydro-1-methyl-ψ-uridine | 97430-85-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 3'-O-acetyl-2'-O-triflyl-4,5'-anhydro-1-methyl-ψ-uridine
• 英文别名: 4,5'-anhydro-3'-O-acetyl-2'-O-triflyl-1-methylpseudouridine；[(1S,10R,11R,12S)-4-methyl-5-oxo-12-(trifluoromethylsulfonyloxy)-8,13-dioxa-4,6-diazatricyclo[8.2.1.02,7]trideca-2,6-dien-11-yl] acetate
• CAS: 97430-85-8
• 化学式: C₁₃H₁₃F₃N₂O₈S
• 分子量: 414.316
• InChiKey: PFVOCQSEZHHSHK-RGOKHQFPSA-N

物化性质

• 沸点：
  476.6±55.0 °C(Predicted)
• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123.02
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-2'-O-triflyl-4,5'-anhydro-1-methyl-ψ-uridine 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以30%的产率得到4,5'-anhydro-1-methyl-5-(2',3'-di-O-acetyl-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Nucleosides. 146. 1-Methyl-5-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil, the C-nucleoside isostere of the potent antiviral agent, 1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)thymine (FMAU). Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides. 6

  摘要：

  The synthesis of 5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil (1, C-FMAU), an isostere of the potent antiviral and antitumor nucleoside 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)thymine (2'-fluoro-5-methyl-ara-U or FMAU), was achieved. Pseudouridine (2) was converted into 4,5'-anhydro-3'-O-acetyl-2'-O-triflylpseudouridine (4), which was treated with tris(dimethylamino)sulfur (1+) difluorotrimethylsilicate (TASF) to give 4,5'-anhydro-5-(3-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1- methyluracil (5b) in 40% yield. Acid hydrolysis of the 4,5'-anhydro linkage of 5b with Dowex 50 (H+) afforded C-FMAU. The inhibitory activity of C-FMAU against HSV-1 and HSV-2 was about 10-fold less than that of FMAU in tissue culture. This compound, however, did not show significant activity in mice inoculated with HSV-1 or HSV-2.

  DOI：

  10.1021/jm00395a023
• 作为产物：
  描述：

  [(1S,10R,11R,12S)-11-hydroxy-4-methyl-5-oxo-8,13-dioxa-4,6-diazatricyclo[8.2.1.02,7]trideca-2,6-dien-12-yl] acetate 生成 3'-O-acetyl-2'-O-triflyl-4,5'-anhydro-1-methyl-ψ-uridine
  参考文献：
  名称：

  PANKIEWICZ, KRZYSZTOF W.;NAWROT, BARBARA;GADLER, HAKAN;PRICE, RICHARD W.;+, J. MED. CHEM., 30,(1987) N 12, 2314-2316

  摘要：

  DOI：

文献信息

• Nucleosides. 132. Synthesis of 5-(2'-substituted-2'-deoxy-.beta.-D-arabinofuranosyl)-1-methyluracils from 1-methyl-.psi.-uridine. The first direct introduction of the 2'-substituent to C-2' in the "up" configuration by nucleophilic reactions. Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides 3
  作者：Krzysztof W. Pankiewicz、Joong Hyup Kim、Kyoichi A. Watanabe

  DOI：10.1021/jo00218a014

  日期：1985.9