Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
J Org Chem. 2010 Mar 5;75(5):1360-5. doi: 10.1021/jo902616s.
The purine nucleoside 2,6-diaminopurine-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-diaminopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O(2)-carbonyl with TMSCl, the N(6)-amino group is protected as the tetramethylsuccinimide (M(4)SI). The O(2)-carbonyl is protected as the DPC derivative, and the trityl group is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.
嘌呤核苷 2,6-二氨基嘌呤-2'-脱氧核苷是通过直接糖基化母体嘌呤杂环 4 的 2,6-双(四甲基琥珀酰亚胺)衍生物与 2-脱氧-3,5-二-O-(对甲苯甲酰基)-α-D-erythro-戊呋喃基氯化物 5 ,使用钠盐法。2'-脱氧异鸟苷是由 2,6-二氨基嘌呤通过五步反应制备的。嘌呤杂环异鸟嘌呤是通过 2,6-二氨基嘌呤的选择性重氮化反应制备的,然后转化为 N9-三苯甲基衍生物以增加溶解度。用 TMSCl 硅烷化 O(2)-羰基后,将 N(6)-氨基保护为四甲基琥珀酰亚胺(M(4)SI)。将 O(2)-羰基保护为 DPC 衍生物,并去除三苯甲基。所得产物以高产率进行糖苷化,生成完全保护的 2'-脱氧异鸟苷。