Chemical synthesis of a-linked alkyl glycosides is often critical in carbohydrate chemistry and glycobiology and can be difficult to achieve for certain sugars.  For instance, the propargyl and allyl glycosides are fundamental building blocks for the 'click chemistry' approach to the construction of microarrays and glycoconjugates. Herein we report a novel 1,2-cis alkyl glycosylation protocol using an unprotected glycosyl thiophenol donor. With the help of excess alcohols (as acceptors) and activation by a Lewis acid/NIS (NBS) system, high yield and a-selectivity are obtained. Also, efficient optimization of the glycosylation conditions was conducted by perdeuterated acetate protection (Ac-d3) of the glycoside substrate as the internal standard. The procedure enables rapid and quantitative evaluation of stereoselectivity and yield by 1H NMR spectroscopy and FIA (flow injection analysis)-ESI-TOF-MS.

Straightforward a-selective alkyl glycosylation from an unprotected thioglycosyl donor: Optimization of conditions using flow-injection analysis and ESI-TOF-MS

246th National Meeting (2013)

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