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

Add time:09/09/2019    Source:sciencedirect.com

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 d-glucose derived 3-N-benzyloxycarbonyl-3-deoxy-1,2-O-isopropylidene-α-d-xylofuranose 8 using intramolecular Mitsunobu reaction as a key step. The glycosidase inhibitory activity of compounds 3–5 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.

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