7-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine | 132235-75-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 7-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine
• 英文别名: 7-[2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl]adenine；[(2S,3R,5R)-5-(6-aminopurin-7-yl)-2-(hydroxymethyl)oxolan-3-yl]methanol
• CAS: 132235-75-7
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: SRBQZRGFMPBQIB-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  ((2S,3R,5R)-5-(6-amino-7H-purin-7-yl)tetrahydrofuran-2,3-diyl)bis(methylene) dibenzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以11%的产率得到7-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV

  摘要：

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.

  DOI：

  10.1021/jo00009a012

文献信息

• SVANSSON, LARS;KVARNSTROM, INGEMAR;CLASSON, BJORN;SAMUELSSON, BERTIL, J. ORG. CHEM., 56,(1991) N, C. 2993-2997
  作者：SVANSSON, LARS、KVARNSTROM, INGEMAR、CLASSON, BJORN、SAMUELSSON, BERTIL

  DOI：——

  日期：——