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Synfacts 2006(4): 0400-0400
DOI: 10.1055/s-2006-932095
DOI: 10.1055/s-2006-932095
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Efficient Acetonation of Sugar Deriavtives
S. Pedatella, A. Guaragna, D. D’Alonzo, M. D. Nisco, G. Palumbo*
Università di Napoli Federico II, Italy
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
24. März 2006 (online)
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.