Potential HIV protease inhibitors: Preparation of di-N-alkylated 2-, 6-, and 2,6-aminodeoxy-derivatives of d-glucose by direct displacement and by a novel reductive-alkylation procedure

Abstract Glucose derivatives carrying branched lipophilic groups at the 2-, 6-, and 2,6-positions were required for biological testing as inhibitors of the protease produced by the human immunodeficiency virus. The synthesis of (N- benzyl -N- ethyl)-2-, 6- and 2,6-diaminodeoxy- d -glucose derivatives is described. The 2- tert -amino group was introduced by a two-step reductive alkylation procedure. The novel tertiary aminosugar, 2,6-di -(N- benzyl -N- ethyl)amino-2,6-dideoxy- d -glucose , was made via direct substitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6 -O- tosyl- d -glucopyranoside with N- benzylethylamine .