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16.17.1.4.4 Method 4: From 5-Aminoimidazole-4-carbonitrile Riboside or 2′-Deoxyriboside

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (200416989.

Nucleobase anion glycosylation of 6-substituted purines yields the N9-nucleosides as the main product. The situation changes if 5-aminoimidazole-4-carbonitrile is used instead of a purine as the precursor; then the main product is 4-amino-1-(ribofuranosyl)-1H-imidazole-5-carbonitrile (AICN-riboside) which is an intermediate in the synthesis of N7-glycosylated purines. Thus, facile conversion of acetylated 4-amino-1-(β-D-ribofuranosyl)-1H-imidazole-5-carbonitrile into 7-ribosylpurine-6-thione 78 is accomplished with diethoxymethyl acetate and hydrogen sulfide in pyridine (Scheme 50).[‌252‌]

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