9-[2-deoxy-β-D-erythro-pentofuranosyl]-6-[[1-(dimethylamino)ethylidene]amino]-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine | 1212821-91-4

• 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: 9-[2-deoxy-β-D-erythro-pentofuranosyl]-6-[[1-(dimethylamino)ethylidene]amino]-2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine
• CAS: 1212821-91-4
• 化学式: C₂₁H₂₉N₇O₅
• 分子量: 459.505
• InChiKey: QGIMWFGSCIMZSC-YNEHKIRRSA-N

反应信息

• 作为产物：
  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