Synthesis of 2-acylamino-2-deoxy-d-glucofuranoses and their transformation into hex-2-enofuranoses

The preparation of 2-deoxy-2-hexanamido (octanamido, decanamido, dodecanamido)-5,6-isopropylidene-d-glucofuranoses (9–12) from the corresponding O-unprotected 2-acylamino-2-deoxy-d-glucopyranoses through the bicyclic glucofurano[2,1-d]oxazolines is reported. Compounds 9–12 are transformed into 2-acylamino-2-deoxy-2-enofuranoses by treatment with Amberlite IRA-400 (OH−) resin.