Acylating properties of N-substituted 2-C:1-N-carbonyl-2-deoxyglucopyranosylamines

Article abstract of DOI:10.1016/0008-6215(94)84114-4

Recently, we reported that the unstable [2+2] cycloadducts of tosyl or trichloroacetyl isocyanate and glycals, upon treatment with alcohols or water, underwent rapid opening of the four-membered ring at the anomeric carbon atom to afford glycosides having alkoxyl and carbamoyl functions located anti. In this paper, we demonstrate that the direction of the attack of nucleophiles at 2-C:1-N-carbonyl-2-deoxyglycopyranosylamines depends on the electronegativity of the Z-substituent at the nitrogen atom. To illustrate this phenomenon, we selected four compounds of α-D-gluco configuration, bearing an N-acyl substituent having less electron-withdrawing character than a sulfonyl or trichloroacetly substituent.