Oligosaccharide synthesis via electrophile-induced activation of glycosyl-n-allylcarbamates

Article abstract of DOI:10.1080/07328309808002350

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.

Full text of DOI:10.1080/07328309808002350

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Journal of Carbohydrate Chemistry
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Oligosaccharide Synthesis via
Electrophile-Induced Activation of
Glycosyl-N-Allylcarbamates
Holger Herzner a , Jörg Eberling a , Michael Schultz a , Jörg Zimmer a
& Horst Kunz a
a Institut für Organische Chemie, Johannes Gutenberg-Universität
Mainz , Becherweg 18, D-55099, Mainz, Germany Phone: Tel.:
06131/392334 Fax: Tel.: 06131/392334 E-mail:
Published online: 22 Aug 2006.
To cite this article: Holger Herzner , Jörg Eberling , Michael Schultz , Jörg Zimmer & Horst Kunz
(1998) Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates ,
Journal of Carbohydrate Chemistry, 17:4-5, 759-776
To link to this article: http://dx.doi.org/10.1080/07328309808002350
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