An explosive growth in the field of glycobiology has stimulated the synthesis of a large number of biologically and therapeutically important glycoconjugates. Due to the complex nature of carbohydrates there is a need for facile and efficient glycosylating agents. Herein, we developed a novel glycosylating agent 3,3-gem-dimethyl-4-pentenyl glycoside that utilizes the Thorpe-Ingold effect to increase reactivity as compared to Fraser�Reid's 4-n-pentenyl glycosyl donor.Our donor serves as both a novel glycosylating agent and anomeric protecting group which is stable under acidic and basic conditions. These donors have been prepared and studied in both glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. We optimized reaction conditions (ie. solvent, activator, temperature, Lewis acid) for both armed and disarmed monosaccharides such as glucose, mannose, galactose and N-phthaloyl glucosamine.

3,3-gem-dimethyl 4-pentenyl glycosides: Novel glycosylating agent and anomeric protecting group

244th National Meeting (2012)

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