Efficient synthesis of the glucosidase inhibitor blintol, the selenium analogue of the naturally occurring glycosidase inhibitor salacinol.
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.
Liu
Hui
H
Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada V5A 1S6.
Pinto
B Mario
BM
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
D004791:Enzyme Inhibitors; D016566:Organoselenium Compounds; D018036:Selenium Compounds; D013402:Sugar Alcohols; D013431:Sulfates; C497875:blintol; C427963:salacinol; D005959:Glucosidases