A Facile Synthesis of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β-d-glucopyranose

Glucosamine derivative 4 ^1–3 is a widely used precursor for syntheses of glucosamine-containing building blocks. A wide range of O-, ^4–6 S- ^7,8 and N-glycosides ^9,10 can be obtained from 4 under Lewis acid catalysis using the corresponding alcohols, thiols, or nitrogenous bases as nucleophiles. Since α-anomer of 4 shows much lower reactivity under these conditions, ^4–10 the use of pure β-anomer of 4 rather than anomeric mixture is preferred. Compound 4 is also a versatile substrate for generating the corresponding glycosyl halides under mild conditions. ^11–13