American Chemical Society

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Preliminary Studies on the Transformation of Nitrosugars into Branched Chain Iminosugars:  Synthesis of 1,4-Dideoxy-4-C-hydroxymethyl- 1,4-imino-pentanols

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posted on 2007-02-15, 00:00 authored by José M. Otero, Raquel G. Soengas, Juan C. Estévez, Ramón J. Estévez, David J. Watkin, Emma L. Evinson, Robert J. Nash, George W. J. Fleet
A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehyde followed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-known glycosidase inhibitor 1,4-dideoxy-1,4-imino-pentanol. This strategy also afforded a new route to some other interesting derivatives, such as N-hydroxy, N-propyloxy, and imino derivatives, a new kind of compounds with promising biological properties.