Sels d'alkyloxyphosphonium—XV: Activation de l'hydroxyle anomere des 2,3,4,6-tetra-o-acyl-d-glucopyranoses—II. Preparation d'orthoesters et de thioglucosides

The joint action of tris(dimethylamino)phosphine (TDAP)-carbon tetrachloride on a tetra-O-acyl-2,3,4,6-d-glucopyranose yields two anomeric oxyphosphonium chlorides (ATDP salts). One of these anomeric forms is stable and the corresponding α-hexafluorophosphate is isolable as a solid. The alcohols react with the mixture of ATDP chlorides to yield 1,2-orthoesters, while thiophenol reacts to give the thioglucoside. These results are discussed and interpreted.