1,2-trans-1-Dihydroxyboryl benzyl S-glycoside as glycosyl donor

• 1,2-trans-1-Dihydroxyboryl benzyl S-glycosides were readily prepared.
• From these compounds, glycosylation with simple alcohols gave pure 1,2-cis-O-glycoside outcome.
• Boronic acid moiety was found essential for the product formation and good anomeric ratio.

Activated by NBS, readily available 1,2-trans-1-dihydroxyboryl benzyl S-glycosides served as glycosyl donors and reacted with certain simple alcohol acceptors to produce pure 1,2-cis-O-glycosides in moderate yields. The boronic acid moiety was revealed essential in the glycosylation for product formation and good anomeric ratio. The preliminary model reactions suggested that glycosyl aryl boronic acids could be used for stereoselective glycosylation.

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