Organic and Biomolecular Chemistry p. 5279 - 5284 (2015)
Update date:2022-08-02
Topics:
Miller, Duncan C.
Carbain, Benoit
Beale, Gary S.
Alhasan, Sari F.
Reeves, Helen L.
Baisch, Ulrich
Newell, David R.
Golding, Bernard T.
Griffin, Roger J.
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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