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Synthesis and structure of d-glucuronolactone derived carboxamides
Saravanan Kandasamy1, George F S Whitehead1, Iñigo J Vitórica-Yrezábal1
1Department of Chemistry, School of Natural Sciences, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
Abstract:
5-O-Protected and 1,2-acetonide-protected D-glucurono-6,3-lactone furanosides were converted into novel furano-glucuronamides through treatment with ammonia. Several O3 protections and O5-deprotection routes afford new primary gluconamide derivatives. However, attempted O3-benzylations of O5-protected intermediates led instead to silyl migration (from O5-TDBMS), competitive N-benzylation or reclosure to the lactone are observed as competing processes. This is not seen the using 5-O-PMB protection which the provides the method of choice for obtaining a fully protection-differentiated glucofuranamide. X-ray crystal structures of a fully-protected glucurono-6,3-lactone lactone and a glucuronamide derivatives are reported.
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