Thioglycosides solid phase synthesis

Glycosylation. The use of DMTST continues to be an important way to activate thioglycosides for the synthesis of polysaccharides and other O-glycosides (e.g., eq 2), including the immobilizing of monosaccharide donors in solid-phase synthesis... 

The stability of thioglycosides in combination with their easy activation makes them highly suitable as donors in most glycosylation strategies and technologies, e.g. in block synthesis as well as in techniques where the donor is manipulated before glycosylation and in solid phase synthesis. 

Since thioglycosides are possible to synthesize with almost any type of protecting group pattern and since they are shelf-stable, they should be very suitable as donors in a commercial approach to solid-phase synthesis of oligosaccharides. That they are excellent donors also in a solid-phase approach is shown, i.e., by the publications from Nicolaou et al. in which up to dodecasaccharides are synthesized on polystyrene beads using thiophenyl and thiomethyl glycoside donors and DMTST as promoter [166, 167]. 

Scheme 1.2 Solid-phase oligosaccharide synthesis employing thioglycosidic linkages to different solid supports.

Thioglycosides have been applied in solid-phase oligosaccharide synthesis by several research groups.29-35 Kahne et al. used them as precursors for the generation of... 

Xu, W., Springfield, S.A. and Koh, J.T. (2000) Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases. Carbohydrate Research, 325,169-176. 

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