title: Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy.
abstract: A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Manuel
authors.initials: M
authors.lastname: Zoidl
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Bernhard
authors.initials: B
authors.lastname: Müller
authors.affiliation: Institute of Inorganic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
authors.forename: Ana
authors.initials: A
authors.lastname: Torvisco
authors.affiliation: Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada.
authors.forename: Christina
authors.initials: C
authors.lastname: Tysoe
authors.affiliation: Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, CNRS-FRE 3517, Université de Picardie Jules Verne, 33 Rue St Leu, 80039 Amiens, France.
authors.forename: Mohamed
authors.initials: M
authors.lastname: Benazza
authors.affiliation: Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, CNRS-FRE 3517, Université de Picardie Jules Verne, 33 Rue St Leu, 80039 Amiens, France. Electronic address: aloysius.siriwardena@u-picardie.fr.
authors.forename: Aloysius
authors.initials: A
authors.lastname: Siriwardena
authors.affiliation: Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada.
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Withers
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria. Electronic address: t.wrodnigg@tugraz.at.
authors.forename: Tanja M
authors.initials: TM
authors.lastname: Wrodnigg
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D050112:Imino Pyranoses / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D050112:Imino Pyranoses; D009570:Nitriles
keywords: C-1-cyano-iminosugar building blocks; Glucocerebrosidase; Glycosidase inhibitor; Iminoalditol; Staudinger/aza Wittig Strecker multicomponent reaction