1,9-dihydro-2-[(4-toluoyl)amino]-9-[2,3,5-tri-O-(4-toluoyl)-β-d-erythro-pentofuranosyl]-6H-purin-6-one

• 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: 1,9-dihydro-2-[(4-toluoyl)amino]-9-[2,3,5-tri-O-(4-toluoyl)-β-d-erythro-pentofuranosyl]-6H-purin-6-one
• 英文别名: [(2R,3R,4R,5R)-5-[2-[(4-methylbenzoyl)amino]-6-oxo-1H-purin-9-yl]-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• 化学式: C₄₂H₃₇N₅O₉
• 分子量: 755.784
• InChiKey: QPKBCDFDIVIWPE-CJEGOSRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,9-dihydro-2-[(4-toluoyl)amino]-9-[2,3,5-tri-O-(4-toluoyl)-β-d-erythro-pentofuranosyl]-6H-purin-6-one 在 对甲苯磺酸 作用下， 以 氯苯 、 乙腈 为溶剂， 反应 2.0h， 以5%的产率得到1,7-dihydro-2-[(4-toluoyl)amino]-7-[2,3,5-tri-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-6H-purin-6-one
  参考文献：
  名称：

  The ThermalN9/N7 Isomerization ofN2-Acylated 2′-Deoxyguanosine Derivatives in the Melt and in Solution

  摘要：

  The protected 2'-deoxyguanosine derivatives 5a - c undergo N-9 --> N-7 isomerization in the melt and in solution, The rate of isomerization is much faster than in the case of the corresponding, ribonucleosides and occurs even in the absence of a catalyst. In the melt (195. 2 min), the N-2.3'-O.5'-O-tris(4-toluoyl) derivative -% and the N-2-acetyl-3',5'-bis-O-[(tert-butyl)dimethylsilyl] derivative 5c gave anomeric mixtures of the,V-isomers 9b/10b) (43%) and 9c/10c (55%). respectively, In addition, the N-9-alpha-D-anomers 8b and 8c are obtained. Different from 5b, the isomerization of peracetylated 5a resulted in low yields. Compound 5b was also prone tu isomerization performed in solution (toluene. 100, 5 min: chlorobenzene, 120. 5 min). furnishing the N-7-regioisomers in 24-53% yield. The highest yield of the N-9 --> N-7 isomerization occurred in the presence of 2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride.

  DOI：

  10.1002/1522-2675(200201)85:1<388::aid-hlca388>3.0.co;2-e
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 鸟苷 以 吡啶 为溶剂， 反应 8.0h， 以41%的产率得到1,9-dihydro-2-[(4-toluoyl)amino]-9-[2,3,5-tri-O-(4-toluoyl)-β-d-erythro-pentofuranosyl]-6H-purin-6-one
  参考文献：
  名称：

  The ThermalN9/N7 Isomerization ofN2-Acylated 2′-Deoxyguanosine Derivatives in the Melt and in Solution

  摘要：

  The protected 2'-deoxyguanosine derivatives 5a - c undergo N-9 --> N-7 isomerization in the melt and in solution, The rate of isomerization is much faster than in the case of the corresponding, ribonucleosides and occurs even in the absence of a catalyst. In the melt (195. 2 min), the N-2.3'-O.5'-O-tris(4-toluoyl) derivative -% and the N-2-acetyl-3',5'-bis-O-[(tert-butyl)dimethylsilyl] derivative 5c gave anomeric mixtures of the,V-isomers 9b/10b) (43%) and 9c/10c (55%). respectively, In addition, the N-9-alpha-D-anomers 8b and 8c are obtained. Different from 5b, the isomerization of peracetylated 5a resulted in low yields. Compound 5b was also prone tu isomerization performed in solution (toluene. 100, 5 min: chlorobenzene, 120. 5 min). furnishing the N-7-regioisomers in 24-53% yield. The highest yield of the N-9 --> N-7 isomerization occurred in the presence of 2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride.

  DOI：

  10.1002/1522-2675(200201)85:1<388::aid-hlca388>3.0.co;2-e

文献信息

• The ThermalN9/N7 Isomerization ofN2-Acylated 2′-Deoxyguanosine Derivatives in the Melt and in Solution
  作者：Bozenna Golankiewicz、Tomasz Ostrowski、Peter Leonard、Frank Seela

  DOI：10.1002/1522-2675(200201)85:1<388::aid-hlca388>3.0.co;2-e

  日期：2002.1

  The protected 2'-deoxyguanosine derivatives 5a - c undergo N-9 --> N-7 isomerization in the melt and in solution, The rate of isomerization is much faster than in the case of the corresponding, ribonucleosides and occurs even in the absence of a catalyst. In the melt (195. 2 min), the N-2.3'-O.5'-O-tris(4-toluoyl) derivative -% and the N-2-acetyl-3',5'-bis-O-[(tert-butyl)dimethylsilyl] derivative 5c gave anomeric mixtures of the,V-isomers 9b/10b) (43%) and 9c/10c (55%). respectively, In addition, the N-9-alpha-D-anomers 8b and 8c are obtained. Different from 5b, the isomerization of peracetylated 5a resulted in low yields. Compound 5b was also prone tu isomerization performed in solution (toluene. 100, 5 min: chlorobenzene, 120. 5 min). furnishing the N-7-regioisomers in 24-53% yield. The highest yield of the N-9 --> N-7 isomerization occurred in the presence of 2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride.