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Synthesis of Conformationally Restricted Glycoamino Acids using Fluorinating Agents
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1  Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado de Correos No. 1203, 41071 Sevilla, Spain

Abstract: A route for the preparation of five- and six-membered ring α/β - and α/γ-glycoamino acids is described starting from D-Glucose. The α/β glycoamino acids were synthesized using a DAST-promoted ring contraction as a key step followed by hydrolysis, acetylation, oxidation and attachment of the α-amino acid. The α/γ-glycoamino acids were synthesized by cleavage of the benzylidene protecting group as the first step, accompanied with subsequent oxidation, acetylation and attachment of the α-amino acid. At the present, we are focusing our attention in synthesizing these α/β-glycoamino acids at a higher scale by using other non-corrosive fluorinating agents.
Keywords: DAST-promoted ring contraction, glycopyranosides, foldamers, glycoamino acids