Synthesis of 1,2,3-triazole-linked glycohybrids in the gluco-, gulo-, and allopyranose series.

[Figure not available: see fulltext.] Ketone derived from diacetone-α-D-glucose is a suitable starting material for the synthesis of 3- C-linked glycohybrids containing 1,2,3-triazole moiety as an intersugar linkage. The pyranose tautomers of 3-deoxy-3-(1,2,3-1 H-triazol-1-yl)glucose, 3- C-[(1,2,3-1 Htriazol-1-yl)methyl]allose and 3- C-[(1,2,3-1 H-triazol-1-yl)methyl]gulose moieties are released upon the acidic hydrolysis of the corresponding O-isopropylidene-protected furanosyl-type synthetic intermediates. Some of the title compounds show a rare property of activating β-galactosidase from Escherichia coli. [ABSTRACT FROM AUTHOR]