2',3'-Dideoxy-2-O-ethyl-3'-fluorouridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2',3'-Dideoxy-2-O-ethyl-3'-fluorouridine
• 英文别名: 1-(2,3-dideoxy-3-fluoro-beta-erythro-pentofuranosyl)-2-ethoxypyrimidin-4(1H)-one；2-ethoxy-1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-4-one
• 化学式: C₁₁H₁₅FN₂O₄
• 分子量: 258.25
• InChiKey: DGGKKQBJAFQUTR-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2',3'-Dideoxy-2-O-ethyl-3'-fluoro-5'-O-(4-phenylbenzoyl)uridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到2',3'-Dideoxy-2-O-ethyl-3'-fluorouridine
  参考文献：
  名称：

  Synthesis of 2-O-ethyl analogues of 3?-azido- and 3?-fluoro-2?,3?-dideoxyuridines and evaluation of their biological activity against HIV

  摘要：

  2-O-Ethyluracil and 2-O-ethylthymine were silylated with 1,1,1,3,3,3-hexamethyldisilazane and condensed in the presence of TMS triflate with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside, 3-azido-2,3-dideoxy-D-erythro-pentofuranoside and 2,3-dideoxy-3-phthalimido-beta-D-erythro-pentofuranose furanose derivatives to give the corresponding 2-O-ethyl nucleosides. Deprotection with saturated methanolic ammonia afforded the 2',3'-dideoxy-3'-fluoro-2-O-ethyluridines whereas 3'-azido-2',3'-dideoxy-3-O-ethyluridine was obtained by deprotection with tetrabutylammonium fluoride in tetrahydrofuran. 3'-Amino-2',3'-dideoxy-3-O-ethyluridine could be obtained only by treatment of the corresponding 3'-azido nucleoside with triphenylphosphine in pyridine. 3'-Deoxy-2-O-ethyl-3'-fluorothymidine (6b) showed moderate activity against HIV-1.

  DOI：

  10.1007/bf00807175

表征谱图