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Synfacts 2006(4): 0400-0400  
DOI: 10.1055/s-2006-932095
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Efficient Acetonation of Sugar Deriavtives

Contributor(s): Yasuhiro Uozumi, Tomohiko Beppu
S. Pedatella, A. Guaragna, D. D’Alonzo, M. D. Nisco, G. Palumbo*
Università di Napoli Federico II, Italy
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Publication History

Publication Date:
24 March 2006 (online)

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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.