Regioisomers in Vorbrüggenʹs guanine nucleoside synthesis; N9 selectivity with a glucosamine derivative and 2-N-acetyl-6-O-diphenylcarbamoylguanine

Vorbrüggen coupling of trimethylsilylated 2-N-acetylguanine with pentofuranose derivatives gives N7/N9 glycosyl mixtures. The N9 isomers can be obtained selectively with 2-N-acetyl-6-O-diphenylcarbamoylguanine, and even with a less reactive glucosamine derivative.