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Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy.
Zoidl, Manuel; Müller, Bernhard; Torvisco, Ana; Tysoe, Christina; Benazza, Mohamed; Siriwardena, Aloysius; Withers, Stephen G; Wrodnigg, Tanja M.
Afiliação
  • Zoidl M; Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
  • Müller B; Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
  • Torvisco A; Institute of Inorganic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria.
  • Tysoe C; Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada.
  • Benazza M; Laboratoire de Glycochimie, des Antimicrobiens et des Agroressources, CNRS-FRE 3517, Université de Picardie Jules Verne, 33 Rue St Leu, 80039 Amiens, France.
  • Siriwardena A; 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.
  • Withers SG; Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C. V6T 1Z1, Canada.
  • Wrodnigg TM; Glycogroup, Institute of Organic Chemistry, Technical University Graz, Stremayrgasse 9, A-8010 Graz, Austria. Electronic address: t.wrodnigg@tugraz.at.
Bioorg Med Chem Lett ; 24(12): 2777-80, 2014 Jun 15.
Article em En | MEDLINE | ID: mdl-24803362
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Imino Piranoses / Nitrilas Idioma: En Ano de publicação: 2014 Tipo de documento: Article
Texto completo
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XML
PubMed Links
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Imino Piranoses / Nitrilas Idioma: En Ano de publicação: 2014 Tipo de documento: Article