The synthesis of polysaccharides through glycosylation, using OH-bearing glycosyl donors as di-functional AB monomers, has achieved limited success with only small molecular weight oligosaccharides obtained.  This is due largely to the low reactivity of the glycosyl donors employed. Unfortunately, the use of a reactive glycosyl donor would result in stability problems.  Herein we report the synthesis polysaccharides through an �in situ� activation approach.  2,3,4-tri-O-acetyl-a-D-Glucosyl and galactosyl bromides were synthesized as the latent AB-monomers.  Upon in situ activation with potent activators, including tetrabutyl ammonium iodide (TBAI) and 4-dimethylamino pyridine (DMAP), polysaccharides with molecular weights up to 9.1 kDa were obtained with narrow PDI.  Additionally, microwave energy was employed to boost the reactivity of the monomers to further increase the molecular weights.

Synthesis of polysaccharides through glycosylation

246th National Meeting (2013)

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