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4,4-(Ethylenedithio)pentanoyl: A masked levulinoyl protective group in the synthesis of oligosaccharides

✍ Scribed by H. J. Koeners; C. H. M. Verdegaal; J. H. van Boom

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
668 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

In this study we demonstrate that the 4,4‐(ethylenedithio)pentanoyl group can be used for the protection of hydroxyl functions of glucose and galactose. Selective acylation of the primary alcoholic function of the galactose derivative 1a was accomplished using 4,4‐(ethylenedithio)pentanoyl chloride. Furthermore, we show that the 4,4‐(ethylenedithio)pentanoyl group can easily be converted into the levulioyl group and that the dithio‐acetal function is stable under the conditions required for the formation of interglycosidic linkages. Finally, a combined use of the levulinoyl and the 4,4‐(ethylenedithio)pentanoyl group enabled us to synthesize a branched tetrasaccharide containing glucose and galactose moieties.

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