Stereoselective synthesis of 2,3-unsaturated-aza-O-glycosides via new diastereoisomeric N-Cbz-imino glycal-derived allyl epoxides |
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| Authors: | Di Bussolo Valeria Fiasella Annalisa Romano Maria Rosaria Favero Lucilla Pineschi Mauro Crotti Paolo |
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| Affiliation: | Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, I-56126 Pisa, Italy. |
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| Abstract: | ![]()
Diastereoisomeric D,L-N-Cbz-imino glycal-derived allyl epoxides 5 and 6 have been synthesized, and their addition reactions with alcohols examined. The reactions lead to the corresponding 2,3-unsaturated-aza-O-glycosides through a new, completely regioselective 1,4-addition process which proceeds with complete substrate-dependent stereoselectivity. |
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