Short and highly stereoselective total synthesis of D-ribo-configured ureido sugars (Articolo in rivista)

Type
Label
  • Short and highly stereoselective total synthesis of D-ribo-configured ureido sugars (Articolo in rivista) (literal)
Anno
  • 2008-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2008.09.080 (literal)
Alternative label
  • Ulgheri Fausta; Giunta Daniela; Spanu Pietro (2008)
    Short and highly stereoselective total synthesis of D-ribo-configured ureido sugars
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Ulgheri Fausta; Giunta Daniela; Spanu Pietro (literal)
Pagina inizio
  • 11768 (literal)
Pagina fine
  • 11775 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://scienceserver.cilea.it/pdflinks/12032618322706210.pdf (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 64 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 8 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 51 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica Biomolecolare del CNR, Trav. La Crucca 3, 07040 Sassari, Italy (literal)
Titolo
  • Short and highly stereoselective total synthesis of D-ribo-configured ureido sugars (literal)
Abstract
  • An highly stereoselective, flexible and very short synthetic approach to D-ribo-configured ureido monosaccharides of the aldose, aldonic acid and alditol series has been performed starting from the 5- (alditol-1-C-yl)-hydantoin intermediates, obtained via aldol-type addition reaction of hydantoin based building blocks to enantiomerically pure aldehydes. A study to assess the stereoselectivity of this reaction has been undertaken and a very high increase of diastereoselectivity was observed depending on the hydantoin protecting group. The imidazolidinone ring elaboration of 5-(alditol-1-C-yl)-hydantoin intermediates to give ureido sugar derivatives was studied. (literal)
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