1-methyl-5-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)uracil | 127517-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-methyl-5-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)uracil
• 英文别名: 5-[(2S,3S,4S,5R)-3-fluoro-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-1-methylpyrimidine-2,4-dione
• CAS: 127517-40-2
• 化学式: C₂₉H₂₇FN₂O₅
• 分子量: 502.542
• InChiKey: ASFDRUSWUHNSKW-RSYZFUPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-methyl-5-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)uracil 在 吡啶 、 叠氮化锂 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 11.0h， 生成 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoro-5-O-trityl-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Nucleosides. 153. Synthesis of 1-methyl-5-(3-azido-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)uracil and 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil. The C-nucleoside isostere of 3'-azido-3'-deoxythymidine and its 2'-"up"-fluoro analog

  摘要：

  1-Methyl-5-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)uracil (C-AZT), a C-nucleoside isostere of the potent anti-AIDS nucleoside 3'-azido-3'-deoxythymidine (AZT), was synthesized. 1-Methyl-2'-deoxy-5'-O-tritylpseudouridine (2a) was oxidized with CrO3/pyridine/Ac2O complex to 1-methyl-5-(5-O-trityl-beta-D-glycero-pentofuranos-3-ulosyl) uracil (12a), which was selectively reduced to 1-methyl-5-(5-O-trityl-beta-D-threo-pentofuranosyl)uracil (13a). Mesylation of 13a to 14a followed by nucleophilic displacement of the mesyloxy group with azide afforded 3'-azido-2',3'-dideoxy-5'-O-trityl-1-methylpseudoridine (15a), which was detritylated to C-AZT. In a similar manner, 1-methyl-5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (C-FMAU, a potent antiherpetic nucleoside) was converted into the 3'-azido analogue (3'-azido-C-FMAU). Both C-AZT and 3'-azido-C-FMAU, however, did not exhibit any significant inhibitory activity against HIV in H9 cells.

  DOI：

  10.1021/jm00169a030
• 作为产物：
  描述：

  5-((2S,3R,5R)-3-Fluoro-4-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-1-methyl-1H-pyrimidine-2,4-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-methyl-5-(2-deoxy-2-fluoro-5-O-trityl-β-D-lyxofuranosyl)uracil
  参考文献：
  名称：

  Nucleosides. 153. Synthesis of 1-methyl-5-(3-azido-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)uracil and 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil. The C-nucleoside isostere of 3'-azido-3'-deoxythymidine and its 2'-"up"-fluoro analog

  摘要：

  1-Methyl-5-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)uracil (C-AZT), a C-nucleoside isostere of the potent anti-AIDS nucleoside 3'-azido-3'-deoxythymidine (AZT), was synthesized. 1-Methyl-2'-deoxy-5'-O-tritylpseudouridine (2a) was oxidized with CrO3/pyridine/Ac2O complex to 1-methyl-5-(5-O-trityl-beta-D-glycero-pentofuranos-3-ulosyl) uracil (12a), which was selectively reduced to 1-methyl-5-(5-O-trityl-beta-D-threo-pentofuranosyl)uracil (13a). Mesylation of 13a to 14a followed by nucleophilic displacement of the mesyloxy group with azide afforded 3'-azido-2',3'-dideoxy-5'-O-trityl-1-methylpseudoridine (15a), which was detritylated to C-AZT. In a similar manner, 1-methyl-5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil (C-FMAU, a potent antiherpetic nucleoside) was converted into the 3'-azido analogue (3'-azido-C-FMAU). Both C-AZT and 3'-azido-C-FMAU, however, did not exhibit any significant inhibitory activity against HIV in H9 cells.

  DOI：

  10.1021/jm00169a030

文献信息

• SOCHACKA, ELZBIETA;NAWROT, BARBARA;PANKIEWICZ, KRZYSZTOF W.;WATANABE, KYO+, J. MED. CHEM., 33,(1990) N, C. 1995-1999
  作者：SOCHACKA, ELZBIETA、NAWROT, BARBARA、PANKIEWICZ, KRZYSZTOF W.、WATANABE, KYO+

  DOI：——

  日期：——