α-1-(3-azido-5-O-benzoyl-2,3-dideoxy-L-threo-pentofuranosyl)thymine | 132979-44-3

• 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: α-1-(3-azido-5-O-benzoyl-2,3-dideoxy-L-threo-pentofuranosyl)thymine
• 英文别名: [(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 132979-44-3
• 化学式: C₁₇H₁₇N₅O₅
• 分子量: 371.352
• InChiKey: VCEFTZVMYBTJNH-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  139.15
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (2E,4R)-5-(benzoyloxy)-4-hydroxy-2-pentenal 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 叔丁基二甲硅基三氟甲磺酸酯 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.75h， 生成 α-1-(3-azido-5-O-benzoyl-2,3-dideoxy-L-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis of L-3'-azido-3'-deoxythymidine (L-AZT) and its stereoisomers

  摘要：

  We report the first synthesis of the L isomer of 3'-azido-3'-deoxythymidine (L-AZT). L-Arabinose was used as starting material for preparation of appropriately protected alpha,beta-unsaturated aldehyde 5. Michael-type addition of azide to 5 gave 3-azido-2,3-dideoxypentofuranoses 7 and 8 suitable for nucleoside coupling with silylated thymine to afford after deprotection L-AZT (11), 1-(3-azido,-2,3-dideoxy-alpha-L-erythro-pentofuranosyl)thymine (12), 1-(3-azido-2,3-dideoxy-beta-L-threo-pentofuranosyl)thymine (13) and 1-(3-azido-2,3-dideoxy-alpha-L-threo-pento-furanosyl)thymine (14). Anti-HIV activity of L-AZT is discussed.

  DOI：

  10.1021/jo00011a026

文献信息

• Synthesis of L-3'-azido-3'-deoxythymidine (L-AZT) and its stereoisomers
  作者：Jesper Wengel、Jesper Lau、Erik B. Pedersen、Carsten M. Nielsen

  DOI：10.1021/jo00011a026

  日期：1991.5

  We report the first synthesis of the L isomer of 3'-azido-3'-deoxythymidine (L-AZT). L-Arabinose was used as starting material for preparation of appropriately protected alpha,beta-unsaturated aldehyde 5. Michael-type addition of azide to 5 gave 3-azido-2,3-dideoxypentofuranoses 7 and 8 suitable for nucleoside coupling with silylated thymine to afford after deprotection L-AZT (11), 1-(3-azido,-2,3-dideoxy-alpha-L-erythro-pentofuranosyl)thymine (12), 1-(3-azido-2,3-dideoxy-beta-L-threo-pentofuranosyl)thymine (13) and 1-(3-azido-2,3-dideoxy-alpha-L-threo-pento-furanosyl)thymine (14). Anti-HIV activity of L-AZT is discussed.