CIHIDECAR 12529
CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Unidad Ejecutora - UE
artículos
Título:
Synthesis and conformational analysis of 1,2-cis fused bicyclic alpha-D-galactofuranosyl thiocarbamate from per-O-tert-butyldimethylsilyl-beta-D-galactofuranosyl isothiocyanate
Autor/es:
LUCIANA BALDONI; CARLOS STORTZ; CARLA MARINO
Revista:
CARBOHYDRATE RESEARCH
Editorial:
ELSEVIER SCI LTD
Referencias:
Año: 2011 vol. 346 p. 191 - 196
ISSN:
0008-6215
Resumen:
Per-O-tert-butyldimethylsilyl-á,â-d-galactofuranosyl isothiocyanate (4) was synthesized by the reaction of per-O-TBS-â-d-galactofuranose (1) with KSCN, promoted by TMSI. Upon O-desilylation (1,2-dideoxy-á-d-galactofuranoso)[1,2d]-1,3-oxazolidine-2-thione (6), the cis-fused bicyclic thiocarbamate was obtained as the only product. Conformational analysis, aided by molecular modelling, showed two stable twist forms (3T4 and 4TO) for the five-membered sugar ring in 6. In aqueous solution, the equilibrium favours the first conformation (3:1 ratio). On the other hand, this ratio decreases for less polar solvents.
