Facile synthesis of 2-O-iodoacetyl protected glycosyl iodides: useful precursors of 1-->2-linked 1,2-trans-glycosides.
Org Lett
; 11(3): 609-12, 2009 Feb 05.
Article
en En
| MEDLINE
| ID: mdl-19175346
The preparation and utilization of novel iodide glycosyl donors, 2-O-iodoacetyl-glycopyranosyl iodides, is described. The mechanism for the reaction of iodine with carbohydrate cyclic ketene acetal was investigated through low-temperature NMR experiments. 2-O-Iodoacetyl-glycopyranosyl iodides can serve as effective glycosyl donors giving 2-O-iodoacetyl 1,2-trans-glycosides in high yields and excellent stereoselectivities. The 2-O-iodoacetyl group was removed selectively with thiourea to afford 2-hydroxy 1,2-trans-glycosides in high yield without affecting other protecting groups and anomeric configurations.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Glicósidos
/
Hidrocarburos Yodados
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2009
Tipo del documento:
Article
Pais de publicación:
Estados Unidos