1212821-93-6Relevant articles and documents
Preparation of the 2′-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation
Arico, Joseph W.,Calhoun, Amy K.,McLaughlin, Larry W.
experimental part, p. 1360 - 1365 (2010/04/30)
Chemical Equetion Presentation 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)-α-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 N6-amino group is protected as the tetramethylsuccinimide (M4SI). The O2-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.
