Synthesis of N-acetylglucosaminyl- and N-acetylgalactosaminylceramides as cerebroside analogs and their anti-human immunodeficiency virus type 1 activities

Monoglycosylceramide derivatives containing mimicks of ceramide were synthesized as cerebroside analogs from D-glucosamine or D-galactosamine derivatives and N-benzyloxycarbonyl-L-serine myristylamide by using trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a promoter. The synthesized sulfate glycolipids show moderate anti-HIV-1 activities.