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- W2119987615 abstract "The synthesis of the first examples of seven-membered ring iminoalditols, molecules displaying an extra hydroxymethyl substituent on their seven-membered ring compared to the previously reported polyhydroxylated azepanes, has been achieved from d-arabinose in 10 steps using RCM of a protected N-allyl-aminohexenitol as a key step. While the (2R,3R,4R)-2-hydroxymethyl-3,4-dihydroxy-azepane 10, a seven-membered ring analogue of fagomine, is a weak inhibitor of glycosidases, the (2R,3R,4R,5S,6S)-2-hydroxymethyl-3,4,5,6-tetrahydroxy-azepane 9 selectively inhibits green coffee bean alpha-galactosidase in the low micromolar range (Ki = 2.2 muM) despite a D-gluco relative configuration." @default.
- W2119987615 created "2016-06-24" @default.
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- W2119987615 date "2004-01-01" @default.
- W2119987615 modified "2023-10-16" @default.
- W2119987615 title "The first synthesis of substituted azepanes mimicking monosaccharides: a new class of potent glycosidase inhibitors" @default.
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- W2119987615 doi "https://doi.org/10.1039/b402542c" @default.
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