Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases?
Organic & Biomolecular Chemistry Pub Date: 2015-03-31 DOI: 10.1039/C5OB00211G
Abstract
Regioselective sulfamoylation of primary hydroxyl groups enabled a 5-step synthesis (overall yield 17%) of the first reported small molecule inhibitor of sulfatase-1 and 2, ((2S,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-((sulfamoyloxy)methyl)tetrahydro-2H-pyran-3-yl)sulfamic acid, which obviated the use of hydroxyl protecting groups and is a marked improvement on the reported 9-step synthesis (overall yield 9%) employing hazardous trifluoromethylsulfonyl azide. The sulfamoylation methodology was used to prepare a range of derivatives of 1, and inhibition data was generated for Sulf-2, ARSA and ARSB.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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