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Approaches to the synthesis of sugar thiolactones
Authors:Jose N. Dominguez  Leonard N. Owen
Affiliation:Department of Chemistry, Imperial College, London SW7 2AZ Great Britain
Abstract:Evidence is presented that aldonolactones undergo “alkyl-oxygen” fission when attacked by thionucleophiles. The reaction of 2,3-O-isopropylidene-d-ery-throno-1,4-lactone with potassium thioacetate gives 2,3-O-isopropylidene-4-thio-d-erythrono-1,4-lactone, the first example of a thiolactone of an aldonic acid. Deacetylation of 5-S-acetyl-2,3-O-isopropylidene-5-thio-d-ribono-1,4-lactone is accompanied by partial migration of sulphur from C-5 to C-4; a mechanism involving an intermediate 5,6-episulphide is suggested.
Keywords:To whom communications should be addressed.
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