Enantiopure tert-butyl 4-oxopipecolic esters were converted to cyclic analogues of bis-homoaspartic acid by Horner-Wadsworth-Emmons olefination and hydrogenation. Condensa-tion of the side chain carboxylic group with anomeric gluco-sylamine and suitable protection of the -amino acid moiety afforded the corresponding N-glucosyl asparagine mimetics as useful building blocks in glycopeptidomimetic synthesis.
New Cyclic Aspartic Acid and N-Glucosyl Asparagine Mimetics / F. M. CORDERO; P. FANTINI; A. BRANDI. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 2006:(2006), pp. 3251-3254. [10.1055/s-2006-951541]
New Cyclic Aspartic Acid and N-Glucosyl Asparagine Mimetics
CORDERO, FRANCA MARIA;BRANDI, ALBERTO
2006
Abstract
Enantiopure tert-butyl 4-oxopipecolic esters were converted to cyclic analogues of bis-homoaspartic acid by Horner-Wadsworth-Emmons olefination and hydrogenation. Condensa-tion of the side chain carboxylic group with anomeric gluco-sylamine and suitable protection of the -amino acid moiety afforded the corresponding N-glucosyl asparagine mimetics as useful building blocks in glycopeptidomimetic synthesis.
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