POTENTIAL HIV PROTEASE INHIBITORS - PREPARATION OF DI-N-ALKYLATED 2-AMINODEOXY-DERIVATIVE, 6-AMINODEOXY-DERIVATIVE, AND 2,6-AMINODEOXY-DERIVATIVE OF D-GLUCOSE BY DIRECT DISPLACEMENT AND BY A NOVEL REDUCTIVE-ALKYLATION PROCEDURE

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 synt hesis of (N-benzyl-N-ethyl)-2-, 6- and 2,6-diaminodeoxy-D-glucose deri vatives is described. The 2-tert-amino group was introduced by a two-s tep reductive alkylation procedure. The novel tertiary aminosugar, -di -(N-benzyl-N-ethyl)amino-2,6-dideoxy-D-glucose, was made via direct su bstitution of the sulphonate group in allyl 2-acetamido-2-deoxy-6-O-to syl-D-glucopyranoside with N-benzylethylamine. (C) 1997 Elsevier Scien ce Ltd.