Free-radical cyclizations onto differently substituted 1,2,3-triazoles installed in sugar templates.
The synthesis and manipulation of differently substituted 1,2,3-triazoles (7-11 and 12-16) installed in sugar templates gave compounds 29-34 and 44-50, after reaction with tributyltin hydride or tris(trimethylsilyl)silane. Following standard procedures compound 44 was transformed into piperidinose derivative 54. These compounds are chiral, useful building blocks for the synthesis of glycosidase inhibitors of the fused-azole piperidinose type.
Marco-Contelles
J
J
Laboratorio de Radicales Libres, IQOG (CSIC), C/ Juan de la Cierva 3, 28006-Madrid, Spain. iqoc2@iqog.csic.es
Rodríguez-Fernández
M
M
D000107:Acetylation; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D005609:Free Radicals; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D006868:Hydrolysis; D007202:Indicators and Reagents; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D005609:Free Radicals; D007202:Indicators and Reagents; D014230:Triazoles; D005959:Glucosidases