Design and synthesis of dimeric heparinoid mimetics

An efficient strategy for the generation of HS-like fragments [GlcA -beta-(1,4)-GlcNAc] and related dimerized (gemini) disaccharides via n-pentynyl glycoside formation is reported. When a convergent synthetic approach was utilized, construction of target molecules was achieved through a combination of chemoselective protection/deprotection protocols, imidate and n-pentenyl glycosylation, and functional group manipulations followed by ozonolysis and reductive amination.