Synthesis of the allo-analogue of trehalose |
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| Authors: | Gordon G Birch Cheang Kuan Lee Anthony C Richardson Ali Yousif |
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| Institution: | National College of Food Technology, University of Reading, St. Georgre''s Avenue, Weybridge, Surrey Great Britain;Department of Chemistry Queen Elizabeth College University of London Campden Hill London W8 7AH Great Britain |
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| Abstract: | Selective benzoylation of HO-2 and HO-2′ of 4,6-O-benzylidene-α-D-glucopyranosyl 4,6-O-benzylidene-α-D-glucopyranoside with N-benzoylimidazole led to the exclusive formation of 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside. Oxidation of either the dibenzoate or the corresponding ditosylate with methyl sulphoxide-phosphorus pentaoxide gave the 3,3′-diulose, and subsequent reduction with borohydride gave the 3,3′diepimers having the allo-allo configuration. De-esterification and hydrolysis of the benzylidene substituents gave α-D-allopyranosyl α-D-allopyranoside. |
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| Keywords: | To whom correspondence should be addressed |
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