Syntheses of fluorine-containing mucin core 2/core 6 structures using novel fluorinated glucosaminyl donors

Syntheses of fluorinated mucin core 6 disaccharides and core 2 trisaccharides modified at the C-3 or C-4 position of the pertinent glucosamine residue required for mechanistic study of glycosyltransferases and sulfotransferases involved in the biosynthesis of O-glycans are reported. Novel fluorinated glucosaminyl donors were synthesized from 2-naphthylmethyl β-d-N-acetylglucosamine (β-O-NAP-GlcNAc) via double inversion of the C-3 or C-4 configuration. A one-step β-alkylation of GlcNAc was reported for the first time to afford β-O-NAP-GlcNAc in high yield, which constitutes the cornerstone of the synthetic strategy based on NAP-glycosides in oligosaccharides synthesis.