Stereoselective One-Pot Synthesis of Constrained N,O-Orthogonally Protected C-Glycosyl Norstatines [C(1')-Aminoglycosyl-1,3-dioxolan-4-ones]. (Articolo in rivista)

Type

• Prodotto della ricerca (Classe)
• Articolo in rivista (Classe)

Label

• Stereoselective One-Pot Synthesis of Constrained N,O-Orthogonally Protected C-Glycosyl Norstatines [C(1')-Aminoglycosyl-1,3-dioxolan-4-ones]. (Articolo in rivista) (literal)

Anno

• 2006-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

• 10.1021/jo0608164 (literal)

Alternative label

• Guerrini, A.; Varchi, G.; Battaglia, A. (2006)
  Stereoselective One-Pot Synthesis of Constrained N,O-Orthogonally Protected C-Glycosyl Norstatines [C(1')-Aminoglycosyl-1,3-dioxolan-4-ones].
  in Journal of organic chemistry
  (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

• Guerrini, A.; Varchi, G.; Battaglia, A. (literal)

Pagina inizio

• 6785 (literal)

Pagina fine

• 6795 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

• 71 (literal)

Rivista

• Journal of organic chemistry (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

• 18 (literal)

Note

• ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

• Laboratory of Chemistry Istituto I.S.O.F.sConsiglio Nazionale delle Ricerche (CNR) Via P. Gobetti, 101, 40129-Bologna, Italy (literal)

Titolo

• Stereoselective One-Pot Synthesis of Constrained N,O-Orthogonally Protected C-Glycosyl Norstatines [C(1')-Aminoglycosyl-1,3-dioxolan-4-ones]. (literal)

Abstract

• A procedure for the synthesis of conformationally constrained C-glycosyl norstatines has been developed. The key step of the reaction is the addition of (S)-N-sulfinyl azomethines to chiral (2S)-enolates of dioxolanones which exploits Seebach's \"SRS\" principle. The trisubstituted C-glycosyl-alpha-hydroxy-beta-aminoacids are formed as N,O-orthogonally protected 1'-glycosyl-sulfinylamino-dioxolan-4-ones, usually with high diastereomeric excesses. Both the sulfinyl group at the nitrogen atom and the acetal moiety of the dioxolanone ring were selectively removed, thus demonstrating the orthogonality of the two protecting groups. In fact, the MeO- induced methanolysis of the acetal group gave the corresponding methyl C-glycosyl-sulfinylamino-isoserinates, while the acid induced removal of the sulfinyl group gave the N-deprotected 1'-glycosylamino-dioxolan-4-ones, which were in several cases subjected to a one-pot base-induced cyclization yielding the corresponding glycosyl-beta-lactams. This allowed the stereochemical configuration assessment of the parent 1'-glycosyl-sulfinylamino-dioxolan-4- ones by chemical correlation methods or by NOE experiments performed on the beta-lactams. (literal)

Prodotto di

• Sintesi e caratterizzazione mediante metodologie chimiche innovative, di scaffold molecolari per l'individuazione di nuove molecole biologicamente attive. (PM.P03.011.002) (Modulo)
• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)

Autore CNR

• GRETA VARCHI (Unità di personale interno)
• ANDREA GUERRINI (Persona)
• ARTURO BATTAGLIA (Unità di personale interno)

Incoming links:

Prodotto

• Institute for organic syntheses and photoreactivity (ISOF) (Istituto)
• Sintesi e caratterizzazione mediante metodologie chimiche innovative, di scaffold molecolari per l'individuazione di nuove molecole biologicamente attive. (PM.P03.011.002) (Modulo)

Autore CNR di

• ARTURO BATTAGLIA (Unità di personale interno)
• GRETA VARCHI (Unità di personale interno)
• ANDREA GUERRINI (Persona)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Journal of organic chemistry (Rivista)