NOUVELLE VOIE D'ACCES AUX 1,2-trans-2-AMINO-2-DESOXY-GLYCOPYRANOSIDES PAR L'INTERMEDIAIRE DES PHOSPHORAMIDATES DE 1,2-trans-2-DESOXY-2-IODOGLYCOPYRANOSYLES

Article abstract of DOI:10.1016/0008-6215(88)80154-X

1,2-trans-2-Deoxy-2-iodoglycopyranosyl phosphoramidates (prepared from the corresponding glycals by addition of iodoazide, followed by Staudinger reaction with a phosphite) led by treatment with an alcohol in the presence of a base to the corresponding 1,2-trans-2-deoxy-2-phosphoramidoglycopyranosides, after inversion of configuration at C-1 and C-2.The reaction proceeded by an aziridine intermediate, which was opened by the alcohol present in the medium.Use of simple alcohols yielded alkyl glycosides having β-D-gluco, β-D-xylo, α-D-manno, and α-D-lyxo configurations, respectively, starting from α-D-manno, α-D-lyxo, β-D-gluco-, and β-D-xylo phosphoramidates, with excellent yields.The same reaction with an alcohol derived from galactopyranose led to the expected disaccharide with a low yield.