N-Mesyl aziridine, I, a new activated vinyl aziridine derived from D-glucal, has been synthesized by cyclization of II with t-BuOK in anhyd. benzene. The reaction of I with alcs., phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N-(mesylamino)-2,3-unsatd.-O-glycosides and disaccharides through a completely regioselective 1,4-addn. process that proceeds with high or complete α-stereoselectivity.
Stereoselective Synthesis of 4-(N-Mesylamino)-2.3-unsaturated-alpha-O-glycosides via a New Glycal-Derived Vinyl alpha-N-(Mesyl)-aziridine
DI BUSSOLO, VALERIA;PINESCHI, MAURO;CROTTI, PAOLO
2005
Abstract
N-Mesyl aziridine, I, a new activated vinyl aziridine derived from D-glucal, has been synthesized by cyclization of II with t-BuOK in anhyd. benzene. The reaction of I with alcs., phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N-(mesylamino)-2,3-unsatd.-O-glycosides and disaccharides through a completely regioselective 1,4-addn. process that proceeds with high or complete α-stereoselectivity.File in questo prodotto:
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