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Regio- and Stereoselectivity in Glycosyl Disulfide Desulfurization. Generation of S-linked Disaccharides
KTH, School of Chemical Science and Engineering (CHE).
2011 (English)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Regio- och stereoselektivitet i desulfurisering av glykosyldisulfider. Framställning av S-länkade disackarider (Swedish)
Abstract [en]

This report describes the synthesis of thiomonosaccharides and the subsequent oxidation to carbohydrate disulfides followed by evaluation of a desulfurization reaction with the aim of developing a facile method for production of S-linked oligosaccharides. The carbohydrate disulfides were synthesized in few steps from commercially available starting materials. Small and simple disulfides were used to evaluate the desulfurization process yielding important information about choice of solvent, catalyst and temperature required for the desulfurization to occur. The optimized conditions were then applied to the carbohydrate disulfides. Results showed that the reactivity of the carbohydrate disulfides depends a lot on the position of the disulfide. One of the carbohydrate disulfides was efficiently desulfurized giving the thioether linked disaccharide, as determined by mass spectrometry. However, more work is needed to develop a general procedure for the desulfurization working on many different carbohydrate disulfides.

Place, publisher, year, edition, pages
2011. , 26 p.
Keyword [en]
Synthesis, Carbohydrate, Disulfide, Desulfurization, Selectivity
National Category
Organic Chemistry
URN: urn:nbn:se:kth:diva-41495OAI: diva2:444901
Subject / course
Organic Chemistry
Educational program
Master of Science - Medical Engineering
Physics, Chemistry, Mathematics
Available from: 2011-10-07 Created: 2011-09-28 Last updated: 2011-11-29Bibliographically approved

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