Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates 1 |
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| Authors: | Holger Herzner Jörg Eberling Michael Schultz Jörg Zimmer Horst Kunz |
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| Institution: | Institut für Organische Chemie, Johannes Gutenberg-Universit?t Mainz , Becherweg 18, D-55099, Mainz, Germany Phone: Tel.: 06131/392334 Fax: Tel.: 06131/392334 E-mail: hokunz@goofy.zdv.uni-mainz.de |
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| Abstract: | Abstract Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl acceptors to form the corresponding oligosaccharides By this method the mucin core 2 trisaccharide2 has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl acceptors can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied. |
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