9-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)adenine | 175544-90-8

• 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: 9-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)adenine
• 英文别名: cordycepin；[(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-methyloxolan-2-yl]methanol
• CAS: 175544-90-8
• 化学式: C₁₁H₁₅N₅O₂
• 分子量: 249.272
• InChiKey: JRAVWEQRTSFOQT-PTZCXBDSSA-N

物化性质

• 沸点：
  526.2±60.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)adenine 以 水 为溶剂， 反应 4.0h， 以83%的产率得到9-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)hypoxanthine
  参考文献：
  名称：

  Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides

  摘要：

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.

  DOI：

  10.1080/07328319608002379
• 作为产物：
  描述：

  (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-methyloxolan-2-ol 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 5.33h， 生成 9-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides

  摘要：

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.

  DOI：

  10.1080/07328319608002379