The double reductive amination of L-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36 %) the galactosidase inhibitor 1-deoxy-D-galactostatin. The aminocyclization of 2,6-di-O-benzyl-L-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric l-deoxyazapyranoses (D-galacto/L-ahro ratio -- 4:1) is obtained in 45-65 % combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxy- 1-benzydrylamino-hexitol (10 % yield) is isolated together with the expected 1-deoxyazasugars of the D-galacto and L-altro series.

Double reductive amination of L-arabino-hexos-5-ulose:a diastereoselective approach to 1-deoxy-D-galactostatin derivatives

CATELANI, GIORGIO;D'ANDREA, FELICIA;
1997

Abstract

The double reductive amination of L-arabino-hexos-5-ulose with benzhydrylamine and NaBH3CN takes place in a diastereospecific manner giving in moderate chemical yield (36 %) the galactosidase inhibitor 1-deoxy-D-galactostatin. The aminocyclization of 2,6-di-O-benzyl-L-arabino-hexos-5-ulose is more complicated giving results dependent from the type of amine: with ammonia or methylamine a mixture of C-5 epimeric l-deoxyazapyranoses (D-galacto/L-ahro ratio -- 4:1) is obtained in 45-65 % combined yield, while with benzhydrylamine substantial amounts of an acyclic 1-deoxy- 1-benzydrylamino-hexitol (10 % yield) is isolated together with the expected 1-deoxyazasugars of the D-galacto and L-altro series.
Barili, Pl; Catelani, Giorgio; Catelani, G; D'Andrea, Felicia; DE RENSIS, F; Puccioni, L.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/204295
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 37
  • ???jsp.display-item.citation.isi??? 39
social impact