2,3-dideoxy-5-O-1-methyl-3-<<5-methyl-4-(1-methylethoxy)-2-pyrimidinyl>oxy>-α-D-xylofuranosyl azide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dideoxy-5-O-1-methyl-3-<<5-methyl-4-(1-methylethoxy)-2-pyrimidinyl>oxy>-α-D-xylofuranosyl azide
• 英文别名: 2-[(2R,3R,5S)-5-azido-2-(propan-2-yloxymethyl)oxolan-3-yl]oxy-5-methyl-4-propan-2-yloxypyrimidine
• 化学式: C₁₆H₂₅N₅O₄
• 分子量: 351.406
• InChiKey: VFZNKGGEUKPVOR-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  三氟甲磺酸异丙酯 、 5'-O-(thexyldimethylsilyl)anhydrothymidine 生成 3'-azido-3'-deoxy-3-isopropylthymidine 、 2,3-dideoxy-3-<<5-methyl-4-(1-methylethoxy)-2-pyrimidinyl>oxy>-α-D-xylofuranosyl azide 、 2,3-dideoxy-5-O-1-methyl-3-<<5-methyl-4-(1-methylethoxy)-2-pyrimidinyl>oxy>-α-D-xylofuranosyl azide 、 3'-azido-3'-deoxy-3-(1-methylethyl)-5'-O-(1-methylethyl)thymidine
  参考文献：
  名称：

  N- versus O-Alkylation of 2,3'-anhydrothymidine: reaction of the obtained pyrimidinium salts with azide ion

  摘要：

  Reaction of 5'-O-(thexyldimethylsilyl)anhydrothymidine (1) with O-(mesitylenesulfonyl)hydroxylamine and CH3OTf generates the pyrimidinium salts 3a and 3b which react with azide ion to give the N3-substituted AZT derivatives 4a and 4b, respectively. In contrast, alkylation of 1 with pentyl triflate occurs at both the N3 and 04 positions leading, after treatment with NaN3, to the expected AZT analog 4d and the novel 3-substituted 2,3-dideoxyxylofuranosyl azide 7d. In a further study, the extent to which competing 04-alkylation occurs was found to be sensitive to steric factors, increasing in the order MeOTf < EtOTf < pentyl OTf < i-PrOTf. Formation of the alternate 04-alkylated AZT derivatives 9 via an intramolecular Hilbert-Johnson process was not observed in these reactions. It was demonstrated, however, that reaction of the intermediate O4-alkylated pyridinium salt 6c with Me4NCl does evolve toward the corresponding C-3' chloro compound 14c. Reaction of 1 with the less reactive alkylating agent (EtO)2P(O)CH2OTf is more complicated producing the O-alkylated product 7f and the novel dimer 19.

  DOI：

  10.1021/jo00063a021