An Efficient Synthesis of 2’-O-(b-D-Glucopyranosyl)- and 2’-O-(2-Acetamido-2-deoxy-b-D-glucopyranosyl)-L-biopterins

Abstract

N 2 -(N,N-Dimethylaminomethylene)-3-[2-(4-nitropheny)ethyl]-1',2'-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-a-D-glucopyranosyl trichloro-acetimidate (9) and l,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2'-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).