Palladium-charcoal-catalyzed reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide: a route to small cluster oligosaccharide mimetics (SCOMs).
Org Lett
; 4(26): 4587-90, 2002 Dec 26.
Article
em En
| MEDLINE
| ID: mdl-12489936
ABSTRACT
[reaction see text] Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac(2)O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.
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Base de dados:
MEDLINE
Assunto principal:
Oligossacarídeos
/
Mimetismo Molecular
/
Fucose
Idioma:
En
Ano de publicação:
2002
Tipo de documento:
Article