Efficient Acetonation of Sugar Deriavtives

Significance

O-Isopropylidene derivatives of sugars were readily prepared by using a triphenylphosphine polymer-bound/I₂ complex. Thus, acetonation reaction of d-glucopyranose took place in the presence of 2 mol equivalents of tri­phenylphosphine polymer-bound/iodine complex to give 1,2:5,6-di-O-isopropylidene-α-d-gluco­furanose in 92% yield within 30 minutes. Eight substrates were examined and the corresponding di-O-isopropylidene derivatives were obtained in 90-95% yield. Mono- and triacetonation reactions were also examined.