2-(acetylamino)-7-{3,5-bis-O-[(tert-butyl)dimethylsilyl]-2-deoxy-α-D-erythro-pentofuranosyl}-1,7-dihydro-6H-purin-6-one | 422308-29-0

• 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: 2-(acetylamino)-7-{3,5-bis-O-[(tert-butyl)dimethylsilyl]-2-deoxy-α-D-erythro-pentofuranosyl}-1,7-dihydro-6H-purin-6-one
• 英文别名: N-[7-[(2S,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-oxo-1H-purin-2-yl]acetamide
• CAS: 422308-29-0
• 化学式: C₂₄H₄₃N₅O₅Si₂
• 分子量: 537.807
• InChiKey: DUGAJMSHTYJBHQ-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(acetylamino)-7-{3,5-bis-O-[(tert-butyl)dimethylsilyl]-2-deoxy-α-D-erythro-pentofuranosyl}-1,7-dihydro-6H-purin-6-one 在 氟化铵 、 甲胺 作用下， 以 甲醇 、 水 为溶剂， 反应 52.0h， 以44%的产率得到7-(2-deoxy-α-D-erythro-pentofuranosyl)-1,7-dihydro-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：

  3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 以 吡啶 为溶剂， 反应 3.03h， 生成 2-(acetylamino)-7-{3,5-bis-O-[(tert-butyl)dimethylsilyl]-2-deoxy-α-D-erythro-pentofuranosyl}-1,7-dihydro-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