Abstract
Synthetic applications of hypervalent iodine reagents in the oxidation state +3 in relation to unsaturated carbohydrates are reviewed. By using the Koser reagent or its bis(azido) derivative, fully protected glycals are oxidatively deblocked in the allylic position. The reaction furnishes carbohydrate-derived 2,3-dihydro-4H-pyranones, which serve as starting materials for the preparation of C-saccharides, glycosyl stannanes or thromboxane A2-analogues. Alternatively, iodine(III) reagents can be used to oxidize halide anions. The halogen-ate complexes thus generated behave like synthetic equivalents of acyl hypobromite and iodite, respectively, or halogen azides, which can all add to alkenes, including glycals, under very mild conditions.
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