Synthesis of erythro and threo furanoid glycals from 1-and 2-phenylselenenyl–carbohydrate derivatives
F Bravo, M Kassou, Y Dı́az, S Castillón - Carbohydrate Research, 2001 - Elsevier
Differently protected erythro and threo furanoid glycals were synthesized by selenoxide
elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions (tBuOOH,
Ti (OiPr) 4, Et2iPrN). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-d-
erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further
reaction with PhSeH in the presence of BF3· Et2O. Erythro and threo furanoid glycals were
also prepared by treating 2-deoxy-2-phenylselenenyl-1, 4-anhydrocyclitols under similar …
elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions (tBuOOH,
Ti (OiPr) 4, Et2iPrN). The phenyl 1-selenoglycosides were obtained from methyl 2-deoxy-d-
erythro-pentofuranoside by protection of the primary hydroxyl or both hydroxyls and further
reaction with PhSeH in the presence of BF3· Et2O. Erythro and threo furanoid glycals were
also prepared by treating 2-deoxy-2-phenylselenenyl-1, 4-anhydrocyclitols under similar …