Carbohydrates thiosugars

Carbohydrate derivatives, in which one or more of the oxygen atoms bonded directly to the carbon skeleton have been replaced by sulfur, are termed thiosugars. The placement of the sulfur atom at the anomeric position constitutes a special case, because thioglycosides, alkyl, aryl and heterocyclic, occupy a very important place as versatile glycosyl donors in glycosidation methodology. Anomeric thiocarbonyl compounds, on the contrary, have been less explored, although their potential and scope is likely to be similar. 

Thiosugars constitute another class of carbohydrate analogs presenting interesting biological and pharmacological properties [105, 106]. 

Ozonation of carbohydrate-based heterocycles containing selenium 111 (or sulfur) afford the corresponding selenoxides 113 (or sulfoxides) <2006JA227>. Low-temperature treatment of the initially formed ozonation products leads to Pummerer-like reactions affording interesting selenosugars 114 (Scheme 7). Thiosugars are formed from the... 

This review describes the synthetic approaches that have been developed since 2000 and summarizes the most important ones developed prior to 2000 [6,7,8,9,10]. It will concentrate on techniques generating enantiomerically enriched or pure carbohydrates and analogs. Aldoses, alditols, and their derivatives will be considered, including aza and thiosugars (with nitrogen and sulfur in the p)ranose or furanose rings). 

Sulfoxides and sulfones have been prepared by oxidation of thiosugars but have only found very limited use as carbohydrate mimics. 

In addition to carbohydrates and alcohols, compounds which also have amine and/or sulfur moieties (e.g., aminoalcohols, aminosugars, thiosugars) rely on the detection of the -OH groups to take advantage of the simplicities of PAD waveforms for Mode I detections. The amine and/or sulfur moieties are exploited to increase the adsorption of the analyte to the electrode surface. Strong adsorption of reacting molecules is considered very beneficial because the residence time of... 

A review on the application of the phosphoramidite method to the synthesis of phosphorylated biomolecules covered, inter alia, mononucleotides, glycosyl phosphates, inositol phosphates and inositol phospholipids. Dibenzyl iVA -diethyl phosphoramidite has been recommended as an efficient and convenient reagent for the preparation of dibenzyl glycosyl phosphites. Bicyclic phosphorylated carbohydrates have been reviewed (40 pp., 60 refs.) in Russian. The rearrangement of a sugar bicyclothiophosphate to a thiosugar bicyclophosphate is covered in Chapter 11. 

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