Journal of the Serbian Chemical Society 2001 Volume 66, Issue 5, Pages: 289-295
https://doi.org/10.2298/JSC0105289H
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Selective desulfonylation in D-xylofuranose 3,5-disulfonates
Hadžić Pavle A. (Faculty of Science, Institute of Chemistry, Novi Sad)
Vukojević Nada S. (Faculty of Science, Institute of Chemistry, Novi Sad)
A method for the preparation of D-xylofuranose derivatives with a free
terminal (C5) alcohol function was developed, starting from
monocyclohexylidene-3,5-disulfonyl- or 5-O-sulfonyl-3-O-methyl ester. The
regioselective displacement of the C5 sulfonyl ester functionwith acetate
ion in dimethylsulfoxide afforded the corresponding
5-O-acetyl-1,2-O-cyclohexylidene-3-O-sulfonyl or 5-O-acetyl-3-O-methyl-
-D-xylofuranose. These esters could be readily hydrolysed into the desired
1,2,3-trisubstituted xylofuranose.
Keywords: D-xylofuranose, sulfonyl ester, nucleophilic substitution, desulfonylation