A concise synthesis of rhamnan (cas 111018-90-7) oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages by iterative α-glycosylation using disaccharide building blocks

Add time:08/22/2019    Source:sciencedirect.com

A concise synthetic route to rhamnan (cas 111018-90-7) oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages is reported. This synthesis was achieved by iterative α-glycosylation using disaccharide building blocks and through orthogonal coupling between thioglycosides of L-rhamnose. To investigate the detailed structure-activity relationship of rhamnan sulfate from Monostroma nitidum against herpes simplex virus type 2, the synthesized oligosaccharides, bearing different orthogonal protecting groups (i.e., benzoyl, benzyl, 2-naphthylmethyl, and/or p-methoxybenzyl) are expected to be suitable for conversion into a range of rhamnan structures with diverse sulfation patterns.

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