title: Efficient synthesis of the glucosidase inhibitor blintol, the selenium analogue of the naturally occurring glycosidase inhibitor salacinol.
abstract: An efficient synthesis of blintol, the selenium congener of the naturally occurring glycosidase inhibitor salacinol, and a potent glucosidase inhibitor itself, is described. Unlike our previously reported synthesis, this improved route makes use of p-methoxybenzyl ether protecting groups in the synthesis of one of the two key intermediates, 2,3,5-tri-O-p-methoxybenzyl-1,4-anhydro-4-seleno-D-arabinitol, from L-xylose. The other key intermediate, 2,4-O-benzylidene-L-erythritol-1,3-cyclic sulfate, was successfully prepared from D-glucose instead of the expensive L-glucose. All protecting groups in the resulting adducts were removed with trifluoroacetic acid to yield a mixture of stereoisomers, thereby obviating the problematic deprotection of benzyl ethers by hydrogenolysis. The major stereoisomer, blintol, was then obtained by fractional crystallization.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada V5A 1S6.
authors.forename: Hui
authors.initials: H
authors.lastname: Liu
authors.forename: B Mario
authors.initials: BM
authors.lastname: Pinto
mesh_terms: D029753:Celastraceae / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013431:Sulfates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D016566:Organoselenium Compounds; D018036:Selenium Compounds; D013402:Sugar Alcohols; D013431:Sulfates; C497875:blintol; C427963:salacinol; D005959:Glucosidases