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Phytosphingosine and its short-chain analog were efficiently synthesized with 19% overall yield in 10 steps, respectively, starting from an inexpensive d-lyxose. Galactosyl donors of sulfide and phosphite types bearing benzoyl protecting groups of 4- and 6-OH underwent glycosylation in excellent α-anomeric selectivity. A variety of α-galactosyl, fucosyl and glucosyl ceramides and serine-type lipids...
Seven-membered iminocyclitols with diverse diastereomers were prepared starting with d- and l-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for β-glucosidase with K i 26.3μM.
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