7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine | 148171-40-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine
• 英文别名: 7-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-6-methoxy-7H-purine；[(2R,3S,5R)-5-(6-methoxypurin-7-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 148171-40-8
• 化学式: C₂₇H₂₆N₄O₆
• 分子量: 502.527
• InChiKey: FLMFFBUSFVCMKB-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-6-methoxy-7H-purine 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 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：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 、 6-甲氧基嘌呤 在 氢氧化钾 、 三(3,6-二氧杂庚基)胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以44%的产率得到9-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-6-methoxy-9H-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