7-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine | 148171-43-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 7-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(6-methoxypurin-7-yl)oxolan-3-ol
• CAS: 148171-43-1
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.257
• InChiKey: YYGCRGXMRNQTKL-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine 在 sodium hydroxide 作用下， 反应 5.0h， 以70%的产率得到7-<2-deoxy-β-D-erythro-pentofuranosyl>-7H-purin-6-one
  参考文献：
  名称：

  Synthesis of 6-Substituted Purine N⁷-(2-Deoxy-β-D-Ribonucleosides) via Anion Glycosylation and Anomerization During the N⁷/N⁹-Glycosyl Transfer

  摘要：

  The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.

  DOI：

  10.1080/15257779508014658
• 作为产物：
  描述：

  7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到7-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine
  参考文献：
  名称：

  Synthesis of 6-Substituted Purine N⁷-(2-Deoxy-β-D-Ribonucleosides) via Anion Glycosylation and Anomerization During the N⁷/N⁹-Glycosyl Transfer

  摘要：

  The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.

  DOI：

  10.1080/15257779508014658