6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine | 1212821-90-3

• 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: 6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine
• 英文别名: 1-[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-3,3,4,4-tetramethylpyrrolidine-2,5-dione
• CAS: 1212821-90-3
• 化学式: C₁₈H₂₄N₆O₅
• 分子量: 404.426
• InChiKey: WZRSSZMSAKBBSJ-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine 、 N,N-二甲基甲酰胺二甲基缩醛 在 甲醇 作用下， 反应 24.0h， 以85%的产率得到9-[2-deoxy-β-D-erythro-pentofuranosyl]-6-[[1-(dimethylamino)ethylidene]amino]-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine
  参考文献：
  名称：

  Preparation of the 2′-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation

  摘要：

  The purine nucleoside 2,6-diamonopurine-2'-deoxyriboside is prepared by the direct glycosylation of the 2,6-bis(tetramethylsuccinimide) derivative of the parent purine heterocycle 4 with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride 5 using the sodium salt method. 2'-Deoxyisoguanosine is prepared from 2,6-diaminopurine by a five-step procedure. The purine heterocycle isoguanine is prepared by selective diazotization of 2,6-diamonopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O-2-carbonyl with TMSCl, the N-6-amino groups is protected as the tetramethylsuccinimide (M4SI). The O-2-carbonyl is protected as the DPC derivative, and the trityl groups is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.

  DOI：

  10.1021/jo902616s
• 作为产物：
  描述：

  9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-2,6-di-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine 在 sodium hydroxide 作用下， 以 吡啶 、 乙醇 、 水 为溶剂， 以72%的产率得到6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine
  参考文献：
  名称：

  Preparation of the 2′-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation

  摘要：

  The purine nucleoside 2,6-diamonopurine-2'-deoxyriboside is prepared by the direct glycosylation of the 2,6-bis(tetramethylsuccinimide) derivative of the parent purine heterocycle 4 with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride 5 using the sodium salt method. 2'-Deoxyisoguanosine is prepared from 2,6-diaminopurine by a five-step procedure. The purine heterocycle isoguanine is prepared by selective diazotization of 2,6-diamonopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O-2-carbonyl with TMSCl, the N-6-amino groups is protected as the tetramethylsuccinimide (M4SI). The O-2-carbonyl is protected as the DPC derivative, and the trityl groups is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.

  DOI：

  10.1021/jo902616s