SYNTHESIS AND TASTE PROPERTIES OF 4,1′, 6′-TRIHALODEOXY SUCROSE ANALOGUES1-2

Abstract

Treatment of 3,4-di-O-acetyl-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O acetyl-4-O-triflyl-α-D-galactopyranoside (3) with a halide source gave, via S _N 2 displacement, the corresponding C-4 halogenated compounds which were subsequently transformed into the monohalogenated 4-deoxy-4-halogenosucrose derivatives, 10–12. Trihalogenated sucrose derivatives, 4-bromo-1′,6′-dichloro 17, 1′,6′-dibromo 18, and 1′,6′-diiodosucrose 19, were synthesized from 5. Exploiting the distinct reactivity at C-1′ and C-6′ trifluoromethanesulfonates enabled the introduction of different halogens at these positions. This pathway led to the preparation of the 4-bromo-1′,6′-dihalodeoxysucrose derivatives, 24–27. Preliminary taste properties of these mono- and tri-halogenated sucrose analogues were also investigated.

ACKNOWLEDGMENTS

We thank the National University of Singapore for financial support under a grant (RP960671) awarded to C.K.L. We also thank L.K. Wong, L. Chen, K.F. Choo and F.Y. Soong and for their assistance in the mass spectra determination and microanalyses.