ISSN:
1434-193X
Keywords:
Carbohydrates
;
Glycals
;
Hypervalent iodine
;
Glycosylation
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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