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. Author manuscript; available in PMC: 2021 Mar 1.
Published in final edited form as: Carbohydr Res. 2019 Dec 19;489:107897. doi: 10.1016/j.carres.2019.107897

Scheme 1.

Scheme 1.

Formation of (a) a 1,2-trans-glycoside via intramolecular rearrangement of an oxocarbenium ion intermediate involving the acyl oxygens at C2, followed by SN2 ring-opening of an acyloxonium ion intermediate involving R’OH, and (b) an orthoester via nucleophilic attack of the acyloxonium ion intermediate by R’OH.