UNPROTECTED SUGAR PHOSPHINIMINES: A FACILE ROUTE TO CYCLIC CARBAMATES OF AMINO SUGARS

Article abstract of DOI:10.1016/S0008-6215(00)90755-9

Unprotected sugar phosphinimines were prepared from various azido sugars by reaction with triphenylphosphine and were converted by carbon dioxide into cyclic carbamates of amino sugars.The reaction could be carried out more conveniently in a one-pot process without isolation of the phosphinimines.The 13C- and 31P-n.m.r. data for N-(β-D-glucopyranosyl)triphenylphosphine imide (2) revealed an unexpected conformation of the phosphinimine moiety (proposed as a "reverse exo-anomeric effect") stabilised by an interaction with HO-2.