Synthetic Applications of Cyclic Sulfites, Sulfates and Sulfamidates in Carbohydrate Chemistry

Alicia      Megia-Fernandez; Julia      Morales-Sanfrutos; Fernando      Hernandez-Mateo; Francisco      Santoyo-Gonzalez

doi:10.2174/138527211794072542

Abstract

Cyclic sulfites, sulfates and sulfamidates derived from saccharides have emerged as valuable and versatile synthons for the preparation of a wide variety of modified sugars and sugar related compounds owing to the combination of the easily and efficient formation of these chemical sulfur derivatives from diols and aminoalcohols with the high chemical stability and enhanced reactivity of those functions towards nucleophiles. The state-of-the-art in this area is covered in the present review using the relative position of the diols and the aminoalcohol functions on the saccharide skeleton and the nature of the nucleophilic reagent (oxygenated nucleophiles, halogens, sulphur nucleophiles, nitrogen nucleophiles, and carbon nucleophiles) as expositive criteria. A comprehensive outlook of the applications of these sulfur derivatives in the preparation of compounds such as azido sugars, halo sugars, thiosugars, pseudo-saccharides, radiotracers, enzymatic inhibitors, anticonvulsant agents, surfactants amongst others is also given.

Keywords: Cyclic sulfites, cyclic sulfates, cyclic sulfamidates, carbohydrates, polyols, diols, aminoalcohols, azido sugars, halo sugars, thiosugars, pseudo-saccharides, radiotracers, enzymatic inhibitors, anticonvulsant agents, O-aryl glycosylation, D-xylopyranose, arabinopyranose, D-Glc, D-Gal, D-Xyl, D-Man, benzocamalexin, selenocyanate, nitrogen nucleophile, 2,2'-anhydronucleosides, 2,3:4,6-disulfite of methyl-Dmannopyranoside, azasugar, carbocyclic nucleosides, 1,1'-sulfonyldiimidazol, Deoxy-2-fluoro-D-glucose, TMAF, TMAOH, TMABr, phenoxide, KSAc, KSCN, isodeoxyuridine, herpes simplex virus, 6-deoxyheptose derivatives, tetraethylammonium fluoride dihydrate, TASF, pseudo-Cdisaccharide, LTD, HIV, hepatitis B viruses, pachastrissamine, D-ribo-phytosphingosine, 3-deoxy-D-manno-2-octulosonic acid, KDO, Niodosuccinimide, iodonium s-dicollidine perchlorate, N-bromosuccinimide, Salacia reticulate, HFIP, kotalanol, 1-1'-sulfonyldiimidazole, L-Rha, D-Rib, N-acetyl-D-allosamine, D-Allo, Lewis X