Acetic acid (E)-1-hydroxymethyl-4,4-dimethoxy-but-2-enyl ester | 136974-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (E)-1-hydroxymethyl-4,4-dimethoxy-but-2-enyl ester
• CAS: 136974-06-6
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: MGPULVULZJYUHH-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (E)-1-hydroxymethyl-4,4-dimethoxy-but-2-enyl ester 在 吡啶 、 盐酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 (2E,4R)-5-(benzoyloxy)-4-hydroxy-2-pentenal
  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
• 作为产物：
  描述：

  (E)-4-O-acetyl-2,3-dideoxy-D-pent-2-enose 、 原甲酸三甲酯 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 Acetic acid (E)-1-hydroxymethyl-4,4-dimethoxy-but-2-enyl ester
  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