1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-methyluracil

• 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: 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-methyluracil
• 英文别名: 1-(3-azido-2,3-deoxy-β-D-erythro-pentofuranosyl)-6-methyluracil；1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: RIJAYUMRJQISSG-LKEWCRSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-甲基尿嘧啶 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 21.0h， 生成 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-6-methyluracil
  参考文献：
  名称：

  Synthesis of an AZT-HEPT Hybrid and Homologous AzddU Derivatives.

  摘要：

  3'-Azido-2',3'-dideoxyuridines 6 and their corresponding cc anomers 5 were synthesized by condensation of silylated 6-alkyl and 5,6-dialkyl substituted uracils 2 with methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-alpha-beta-D-erythro-pentofuranoside (4). Compounds 5 and 6 were treated with tetrabutylammonium fluoride to obtain the deprotected nucleosides 7 and 8, respectively.

  DOI：

  10.3891/acta.chem.scand.50-0417

文献信息

• HREBABECKY, HUBERT;HOLY, ANTONIN;DE, CLERCQ ERIK, COLLECT. CZECHOSL. CHEM. COMMUN., 55,(1990) N, C. 1801-1811
  作者：HREBABECKY, HUBERT、HOLY, ANTONIN、DE, CLERCQ ERIK

  DOI：——

  日期：——
• Hrebabecky, Hubert; Holy, Antonin; Clercq, Erik de, Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 7, p. 1801 - 1811
  作者：Hrebabecky, Hubert、Holy, Antonin、Clercq, Erik de

  DOI：——

  日期：——
• Synthesis of an AZT-HEPT Hybrid and Homologous AzddU Derivatives.
  作者：Erik Larsen、Krzysztof Danel、Gitte B. Vaaben、Ali A. El-Emam、Erik B. Pedersen、Claus Nielsen、Shu Hai Zhao、Mauro I. Ciglic、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0417

  日期：——

  3'-Azido-2',3'-dideoxyuridines 6 and their corresponding cc anomers 5 were synthesized by condensation of silylated 6-alkyl and 5,6-dialkyl substituted uracils 2 with methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-alpha-beta-D-erythro-pentofuranoside (4). Compounds 5 and 6 were treated with tetrabutylammonium fluoride to obtain the deprotected nucleosides 7 and 8, respectively.