title: Preliminary studies on the transformation of nitrosugars into branched chain iminosugars: synthesis of 1,4-dideoxy-4-C-hydroxymethyl-1,4-imino-pentanols.
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].
authors.affiliation: Departamento de Química OrgAnica, Universidade de Santiago, 15782 Santiago de Compostela, Spain.
authors.forename: José M
authors.initials: JM
authors.lastname: Otero
authors.forename: Raquel G
authors.initials: RG
authors.lastname: Soengas
authors.forename: Juan C
authors.initials: JC
authors.lastname: Estévez
authors.forename: Ramón J
authors.initials: RJ
authors.lastname: Estévez
authors.forename: David J
authors.initials: DJ
authors.lastname: Watkin
authors.forename: Emma L
authors.initials: EL
authors.lastname: Evinson
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Nash
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
mesh_terms: D000478:Alkylation; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005557:Formaldehyde; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000494:pharmacology*; D007202:Indicators and Reagents; D008958:Models, Molecular; D009574:Nitro Compounds / Q000138:chemical synthesis*; D000439:Pentanols / Q000138:chemical synthesis* / Q000494:pharmacology*; D011759:Pyrrolidines / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D004791:Enzyme Inhibitors; D050111:Imino Sugars; D007202:Indicators and Reagents; D009574:Nitro Compounds; D000439:Pentanols; D011759:Pyrrolidines; D005557:Formaldehyde; D006026:Glycoside Hydrolases