Acetate protecting groups, addition, iodine

Additional examples of synthetic application of periodic acid as an oxidant include the oxidative iodination of aromatic compounds [1336-1341], iodohydrin formation by treatment of alkenes with periodic acid and sodium bisulfate [1342], oxidative cleavage of protecting groups (e.g., cyclic acetals, oxathioacetals and dithioacetals) [1315, 1343], conversion of ketone and aldehyde oximes into the corresponding carbonyl compounds [1344], oxidative cleavage of tetrahydrofuran-substituted alcohols to -y-lactones in the presence of catalytic PCC [1345] and direct synthesis of nitriles from alcohols or aldehydes using HsIOe/KI in aqueous ammonia [1346],... 

They also demonstrated that inexpensive molecular iodine can be used as a cheap, nontoxic, general, and fast catalyst for one-pot tandem acetalation-esteri-fication reactions of glycosides in good to excellent yields without the need of purification after every reaction step. Further, the addition of catalytic DMAP can be used to accelerate the esterification step and thus shorten the reaction times. The method is mild and compatible with different thioglycosides and 0-glycosides, applicable to the formation of 4,6-0-benzylidene and 4,6-0-p-methoxybenzylidene acetals in tandem reaction with either 2,3-0-di-acetate or 2,3-0-di-benzoate esters and also amenable to commonly used amino-protecting groups (e.g., phthalimides and 2,2,2-trichloroethoxycarbonyl chloride). 

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