Design and synthesis of hyaluronan-mimetic gemini disaccharides

An efficient strategy has been designed for the preparation of synthetic mimics of hyaluronan (HA, ) and its dimerized (Gemini) disaccharides () via n-pentenyl glycoside formation. Construction of the target molecules was achieved through a combination of protection/deprotection protocols, imidate glycosylation methodology followed by ozonolysis, and reductive amination. These tailored synthetic mimics could act as versatile building blocks with therapeutic applications in tissue engineering, treatment of cancer and as drug delivery agents.