Die ungewöhnliche Reaktion von 1.2—5.6-Di-O-isopropyliden-α-D-glucofuranose (Diacetonglucose) mit dem System Triphenylphosphin/Azodicarbonsäureester / The Unusual Reaction of 1,2-5,6-Di-O-isopropylidene Glucofuranose (Diacetoneglucose) with the System Triphenylphosphine/Azodicarboxylate

Abstract

The 1,2-5,6-Di-O-isopropylidene glucofuranose (7) reacts with triphenylphosphine/azodicarboxylate and methyliodide with formation of the relatively stable alkoxyphosphonium salt (8a). With water and alcohols 8 forms triphenylphosphine oxide and diacetone glucose 7. The reaction of 8 with sodium benzoate gives the glucofuranose-3-benzoat (10), the formal product of substitution under retention of configuration.