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. 2005 May 12;7(10):2007-10.
doi: 10.1021/ol050491y.

Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis

Leendert J van den Bos  1 , Remy E J N Litjens, Richard J B H N van den Berg, Herman S Overkleeft, Gijsbert A van der Marel
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Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis

Leendert J van den Bos et al. Org Lett. .

Abstract

The chemo- and regioselective TEMPO/BAIB-mediated oxidation of 2,6- and 3,6-dihydroxy 1-thio glycopyranosides to the corresponding 1-thio uronic acid lactones is described. These locked 1-thio glycuronides can directly be used as donors in glycosidation reactions using the Ph(2)SO/Tf(2)O reagent system. Alternatively, selective opening of the lactone bridge liberates a hydroxyl function for ensuing glycosylations.

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