Carbohydrate Research p. 1 - 4 (2016)
Update date:2022-07-30
Topics:
Szabó, Lajos Z.
Hanrahan, Dillon J.
Jones, Evan M.
Martin, Erin
Pemberton, Jeanne E.
Polt, Robin
Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.
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