Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine (Articolo in rivista)

Type

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

Label

• Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine (Articolo in rivista) (literal)

Anno

• 2002-01-01T00:00:00+01:00 (literal)

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

• 10.1002/1099-0690(200203)2002:5<873::AID-EJOC873>3.0.CO;2-V (literal)

Alternative label

• Guarna, Antonio; Cini, Nicoletta; Machetti, Fabrizio; Menchi, Gloria; Occhiato, Ernesto Giovanni (2002)
  Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine
  in European journal of organic chemistry (Print)
  (literal)

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

• Guarna, Antonio; Cini, Nicoletta; Machetti, Fabrizio; Menchi, Gloria; Occhiato, Ernesto Giovanni (literal)

Pagina inizio

• 873 (literal)

Pagina fine

• 880 (literal)

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

• http://onlinelibrary.wiley.com/doi/10.1002/1099-0690(200203)2002:5%3C873::AID-EJOC873%3E3.0.CO;2-V/abstract (literal)

Rivista

• European journal of organic chemistry (Rivista)

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

• 8 (literal)

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

• 5 (literal)

Note

• ISI Web of Science (WOS) (literal)
• Scopu (literal)

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

• Centro di studio della chimica e della struttura dei composti eterociclici del CNR, Dipartimento di chimica Organica 'Ugo Schiff' dell'Università di Firenze (literal)

Titolo

• Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine (literal)

Abstract

• The synthesis of the new N-Fmoc-protected dipeptide isoster methyl (IS,2S,5S,6R)-2exo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate (BTS) has been achieved, starting from (R,R)-tartaric acid and O-benzyl-L-serine, in 11% overall yield after 9 steps. Interestingly, starting from the same a-amino acid, it Was also possible to prepare the 2endo-substituted compound, formally derived from the combination of tartaric acid with D-serine. Each compound has a CH2OH functional group at C-2, which is very useful for greater diversification of the 7,8-dioxa-3-azabicyclof 3.2.1] octane-6-carboxylate (BTAa) dipeptide isosters, The oxidation of the C-2 carbinol group in BTS, moreover, gave rise to a novel, conformationally constrained, alpha-amino acid that may find application in peptidomimetic synthesis (literal)

Prodotto di

• Istituto di chimica dei composti organo metallici (ICCOM) (Istituto)
• Nuove metodologie sintetiche per la funzionalizzazione molecolare in ambiente biologico (PM.P01.012.002) (Modulo)

Autore CNR

• ANTONIO GUARNA (Persona)
• FABRIZIO MACHETTI (Unità di personale interno)

Insieme di parole chiave

• Keywords of "Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto di chimica dei composti organo metallici (ICCOM) (Istituto)
• Nuove metodologie sintetiche per la funzionalizzazione molecolare in ambiente biologico (PM.P01.012.002) (Modulo)

Autore CNR di

• FABRIZIO MACHETTI (Unità di personale interno)
• ANTONIO GUARNA (Persona)

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

• European journal of organic chemistry (Rivista)

Insieme di parole chiave di

• Keywords of "Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine" (Insieme di parole chiave)