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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Authors: | Otero José M Soengas Raquel G Estévez Juan C Estévez Ramón J Watkin David J Evinson Emma L Nash Robert J Fleet George W J |
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Institution: | Departamento de Química OrgAnica, Universidade de Santiago, 15782 Santiago de Compostela, Spain. |
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Abstract: | 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. reaction: see text]. |
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