Synthesis of polyhydroxylated azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from d-glucose. Issue 31 (5th August 2015)

• Record Type: Journal Article
• Authors: Lawande, Pravin P.; Sontakke, Vyankat A.; Nair, Roopa J.; Khan, Ayesha; Sabharwal, Sushma G.; Shinde, Vaishali S.
• Is Part Of: Tetrahedron. Volume 71:Issue 31(2015)
• Page Start: 5085
• Page End: 5090
• Publication Date: 2015-08-05
• Subjects: Azetidine -- Iminosugars -- Glycosidase inhibitory activity -- Mitsunobu reaction -- d-Glucose; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.05.057
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The azetidine iminosugars, (2 S, 3 R )-2-(( R )-1, 2-dihydroxyethyl)azetidin-3-ol3, (2 R, 3 R )-2-(hydroxymethyl)azetidin-3-ol4, and (2 S, 3 R )-3-hydroxy- N -methylazetidine-2-carboxylic acid5 were synthesized fromd -glucose derived 3- N -benzyloxycarbonyl-3-deoxy-1, 2- O -isopropylidene-α-d -xylofuranose8 using intramolecular Mitsunobu reaction as a key step. The glycosidase inhibitory activity of compounds3 –5 was screened against various enzymes. Amongst all synthesized compounds, the N -methylated compound5 exhibited significant inhibitory activity against amyloglucosidase from Aspergillus niger in micro molar range. Graphical abstract: