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- W2950682015 abstract "Short, efficient, and stereoselective syntheses of enantiomerically pure C-3- and C-4-alkylated analogues of (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine, a potent α-galactosidase inhibitor, from 4-hydroxy-l-proline are presented. Grignard addition or enolate alkylation of a N-(9-phenylfluoren-9-yl)-4-oxo-3-[(methoxymethyl)oxy]proline and epoxidation or hydroboration of a 4-methylene-3-[(methoxymethyl)oxy]proline proceeded with complete stereoselection and in excellent yields. The inhibitory activities of the synthesized pyrrolidines were measured and showed that the fit of A. niger α-galactosidase and the jack bean α-mannosidase around C-3 of the pyrrolidine ring (α face) must be very tight, while the fit around C-4 (α face) is much looser. Positioning a methylene group between the hydroxyl at C-4 and the pyrrolidine ring completely abolishes the inhibitory activity (see analogue 5)." @default.
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- W2950682015 date "1998-04-22" @default.
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- W2950682015 title "C-3- and C-4-Alkylated Polyhydroxypyrrolidines: Enantiospecific Syntheses and Glycosidase Inhibitory Activity" @default.
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- W2950682015 doi "https://doi.org/10.1021/jo980078m" @default.
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