Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof (Articolo in rivista)

Type

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

Label

• Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof (Articolo in rivista) (literal)

Anno

• 2002-01-01T00:00:00+01:00 (literal)

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

• 10.1021/jo0257905 (literal)

Alternative label

• Gloria Rassu, Luciana Auzzas, Luigi Pinna, Vincenzo Zambrano, Franca Zanardi, Lucia Battistini, Lucia Marzocchi, Domenico Acquotti, Giovanni Casiraghi (2002)
  Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof
  in Journal of organic chemistry (Online); ACS, American chemical society, Washington, DC (Stati Uniti d'America)
  (literal)

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

• Gloria Rassu, Luciana Auzzas, Luigi Pinna, Vincenzo Zambrano, Franca Zanardi, Lucia Battistini, Lucia Marzocchi, Domenico Acquotti, Giovanni Casiraghi (literal)

Pagina inizio

• 5338 (literal)

Pagina fine

• 5342 (literal)

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

• http://pubs.acs.org/doi/abs/10.1021/jo0257905 (literal)

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

• 67 (literal)

Rivista

• Journal of organic chemistry (Rivista)

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

• 5 (literal)

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

• 15 (literal)

Note

• ISI Web of Science (WOS) (literal)

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

• Vincenzo Zambrano, Gloria Rassu, Luciana Auzzas (literal)

Titolo

• Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof (literal)

Abstract

• A chiral, divergent synthesis of two carbafuranosylamines, 1 and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-d-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields. (literal)

Editore

• ACS, American chemical society (Editore)

Prodotto di

• Istituto di chimica biomolecolare (ICB) (Istituto)

Autore CNR

• VINCENZO ZAMBRANO (Persona)
• LUCIANA AUZZAS (Persona)
• GLORIA MARIA RITA RASSU (Unità di personale interno)

Insieme di parole chiave

• Parole chiave di "Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof" (Insieme di parole chiave)

Incoming links:

Autore CNR di

• LUCIANA AUZZAS (Persona)
• GLORIA MARIA RITA RASSU (Unità di personale interno)
• VINCENZO ZAMBRANO (Persona)

Prodotto

• Istituto di chimica biomolecolare (ICB) (Istituto)

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

• Journal of organic chemistry (Rivista)

Editore di

• ACS, American chemical society (Editore)

Insieme di parole chiave di

• Parole chiave di "Variable Strategy toward Carbasugars and Relatives. 4. Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof" (Insieme di parole chiave)