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Synthesis of Potential Inhibitors of Glycosidases and Glycohydrolases. 1. 1,4-Imino-1,4-dideoxyribose

M.E. Hassan and J.T. Slama

Department of Chemistry, Faculty of Science, The African University, Aswan, Egypt


Abstract: A stereoselective synthesis of D or L form of 1,4-imino-1,4-dideoxyribose has been achieved by two different approaches. The first begins with resolution of the inexpensive 3,4-dehydroproline. Key steps are a stereoselective dihydroxylation followed by reduction of the carboxylate group to a hydroxymethyl. Alternately, 4-tosyl-2,3-O-isopropylidene derivatives of D- or L-lyxose were converted to the azides. Acid hydrolysis of the methyl glycoside followed by catalytic hydrogenation produces 1,4-imino-1,4-dideoxyribose. These aminoribose derivatives should serve as the basis for the development of specific inhibitors of glycosidases and potentially of NAD glycohydrolases.

Full paper in Portable Document Format: 464a261.pdf


Chemical Papers 46 (4) 261–265 (1992)

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