Stereoselective synthesis of 4-(N-mesylamino)-2,3-unsaturated- alpha-O-glycosides via a new glycal-derived vinyl alpha-N-(mesyl)-aziridine |
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Authors: | Di Bussolo Valeria Romano Maria Rosaria Pineschi Mauro Crotti Paolo |
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Institution: | Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy. |
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Abstract: | reaction: see text] N-Mesyl aziridine 7alpha, a new activated vinyl aziridine derived from d-glucal, has been synthesized by cyclization of trans-N,O-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N-(mesylamino)-2,3-unsaturated-O-glycosides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity. |
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