Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone

P V Murphy, C McDonnell, L Hamig, D E Paterson, R J K Taylor

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Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra-O-(tert-butyldimethylSilyl)-D-glucono-1,4-lactone, obtained in 84% yield from the reaction of glucono-1,5-lactone with TBSOTf and lutidine in dichloromethane, has been confirmed by X-ray crystallography. Formation of the glucono-1,5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo-glycal derivatives of these lactones using the Ramberg-Backlund rearrangement of the corresponding sulfones. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)79-85
Number of pages7
Issue number1
Publication statusPublished - 6 Jan 2003



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