A concise synthesis of rhamnan oligosaccharides with alternating alpha-(1 -> 2)/(1 -> 3)-linkages and repeating alpha-(1 -> 3)-linkages by iterative alpha-glycosylation using disaccharide building blocks

作者：Tanaka Hidenori^*; Hamaya Yu; Nishiwaki Nagatoshi; Ishida Hideharu

来源：Carbohydrate Research, 2018, 455: 23-31.

DOI：10.1016/j.carres.2017.11.005

• Rhamnan oligosaccharide
• Iterative alpha-glycosylation
• Orthogonal coupling
• Rhamnan sulfate
• Monostroma nitidum
• Herpes simplex virus type 2

A concise synthetic route to rhamnan oligosaccharides with alternating alpha-(1 -> 2)/(1 -> 3)-linkages and repeating alpha-(1 -> 3)-linkages is reported. This synthesis was achieved by iterative a-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.

• 出版日期2018-1-2