Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives (Articolo in rivista)

Type
Label
  • Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives (Articolo in rivista) (literal)
Anno
  • 1991-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo00023a015 (literal)
Alternative label
  • Giovanni Casiraghi, Lino Colombo, Gloria Rassu, and Pietro Spanu (1991)
    Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives
    in Journal of organic chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Giovanni Casiraghi, Lino Colombo, Gloria Rassu, and Pietro Spanu (literal)
Pagina inizio
  • 6523 (literal)
Pagina fine
  • 6527 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 56 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica dell'Uniuersita' and Istituto per l'Applicazione delle Tecniche Chimiche Avanzate ai Problemi Agrobiologici del CNR, I-07100 Sassari, Italy (literal)
Titolo
  • Total Synthesis of 6-Deoxy-6-aminoheptopyranuronic Acid Derivatives (literal)
Abstract
  • Two enantio couples of terminal C-glycopyranosyl alfa-amino acids, namely the aminopyranuronic acids L-9, D-9 and L-10, D-10, have been synthesized from the serine-derived pair L-2, D-2 by exploiting enantiomerically pure butenolide intermediates 3 and 4. The key synthetic steps involved the sequential antiselective cis dihydroxylation of the butenolide double bond and the clean furanose-to-pyranose ring expansion to construct the sugar skeleton with the proper stereochemistry. In our best performance, homogeneous L-9 was prepared from L-2 in four steps and 10 reactions in 20% overall yield. (literal)
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