An efficient synthetic route to O-(2-O-benzyl-3,4-di-O-acetyl-α/β-l-fucopyranosyl)-trichloroacetimidate.

An efficient synthetic route to prepare O-(2-O-benzyl-3,4-di-O-acetyl-α/β-l-fucopyranosyl)-trichloroacetimidate from l-fucose was developed by introducing the thiophenyl group at the anomeric center and the benzylidene functional group to protect the 3 and 4 positions. Although three approaches were considered, the best result was obtained when, after the 2-hydroxyl benzylation, both protective groups were simultaneously removed by using acetic anhydride and perchloric acid supported on silica as catalyst. Selective deacetylation of the obtained tri-O-acetate followed by the reaction of the resultant hemiacetal with trichloroacetonitrile and DBU afforded the trichloroacetimidate with an overall yield of 56% from the l-fucose.