Synthesis of polyhydroxylated azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from d-glucose

The azetidine iminosugars, (2S,3R)-2-((R)-1,2-dihydroxyethyl)azetidin-3-ol 3 ,( 2R,3R)-2-(hydroxymethyl) azetidin-3-ol 4, and (2S,3R)-3-hydroxy-N-methylazetidine-2-carboxylic acid 5 were synthesized from Dglucose derived 3-N-benzyloxycarbonyl-3-deoxy-1,2-O-isopropylidene-a-D-xylofuranose 8 using intramolecular Mitsunobu reaction as a key step. The glycosidase inhibitory activity of compounds 3e5 was screened against various enzymes. Amongst all synthesized compounds, the N-methylated compound 5 exhibited significant inhibitory activity against amyloglucosidase from Aspergillus niger in micro molar range.