First Synthesis of a Representative, Natural Pterin Glycoside: 2’-O-(α-D-Glucopyranosyl)biopterin

Glycosylation of N(2)-(N,N-dimethylaminomethylene)-1’-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl) ethyl]biopterin (14) with the novel donor 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-D-glucopyranosyl bromide (19) in the presence of silver triflate and tetramethylurea predominantly afforded the corresponding α-D-glucopyranoside (20a), from which 2’-O-(α-D-glucopyranosyl)biopterin (1) was obtained by the successive removal of the protecting groups.