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- W2039587056 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." @default.
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- W2039587056 date "2004-12-23" @default.
- W2039587056 modified "2023-10-17" @default.
- W2039587056 title "Efficient Synthesis of the Glucosidase Inhibitor Blintol, the Selenium Analogue of the Naturally Occurring Glycosidase Inhibitor Salacinol" @default.
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- W2039587056 doi "https://doi.org/10.1021/jo048058+" @default.
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