The stereospecific O-glycosylation of alcs., phenol, and partially protected monosaccharides with the diastereoisomeric D-allal and D-galactal-derived N-nosyl aziridines I and II leads to the corresponding 4-N-(nosylamino)-2,3-unsatd.-α-O-glycosides, e.g. III (R1 = OMe, R2 = H), and β-O-glycosides, e.g. III (R1 = H, R2 = OMe), resp.  The N-(nosylamino) group of 4-N-(nosylamino)-2,3-unsatd.-α-O- and β-O-glycosides can easily be deprotected to give the corresponding 4-amino-2,3-unsatd.-O-glycosides.

N-Nosyl as a stereoselectivity-improving and easily removable group in the O-glycosylation of D-allal and D-galactal-derived allyl aziridines. Stereospecific synthesis of 4-amino-2,3-unsaturated-O-glycosides

DI BUSSOLO, VALERIA;PINESCHI, MAURO;CROTTI, PAOLO
2007-01-01

Abstract

The stereospecific O-glycosylation of alcs., phenol, and partially protected monosaccharides with the diastereoisomeric D-allal and D-galactal-derived N-nosyl aziridines I and II leads to the corresponding 4-N-(nosylamino)-2,3-unsatd.-α-O-glycosides, e.g. III (R1 = OMe, R2 = H), and β-O-glycosides, e.g. III (R1 = H, R2 = OMe), resp.  The N-(nosylamino) group of 4-N-(nosylamino)-2,3-unsatd.-α-O- and β-O-glycosides can easily be deprotected to give the corresponding 4-amino-2,3-unsatd.-O-glycosides.
2007
DI BUSSOLO, Valeria; M. R., Romano; Pineschi, Mauro; Crotti, Paolo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/179572
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