Thioglycosides 1- 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Carbohydrate derivatives, in which one or more of the oxygen atoms bonded directly to the carbon skeleton have been replaced by sulfur, are termed thiosugars.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. 

J. M. Lacombe, N. Rakotomanomana, and A. A. Pavia, Free-radical addition of 1-thiosugars to alkenes. A new general approach to the synthesis of 1-thioglycosides, Tetrahedron Lett., 29 (1988) 4239-4296. 

Ethyl 2,3,4-tri-0-acetyl-l-thio- 3-L-rhamnopyranoside has been prepared by way of the diethyldithioacetal, and the cysteamine 5-glucuronide (70) was obtained both by use of a glyuronosyl bromide derivative and by treatment of a 1-thiosugar derivative with 2-bromoethylamine. 5-Benzyl thioglycosides of... 

Radical addition of a 1-thiosugar to an alkene has been used in the preparation of a number of thioglycosides as exemplified in Scheme 4 with regard to the anomeric configuration of the... 

The thioglycoside antibiotic clindamycin-2-phosphate 29 has three separate molecules in the crystal, differing mainly in the orientation of the phosphate group and the pyrrolidinyl moiety. Thiosugar glycoside 30 and bis(2,3,4,6-tetra-0-acetyl-P-D-glucopyranosyl)diselenide and disulfide. ... 

---