OLIGOSACCHARIDE SYNTHESIS VIA ELECTROPHILE-INDUCED ACTIVATION OF GLYCOSYL-N-ALLYLCARBAMATES

Authors
HERZNER H EBERLING J SCHULTZ M ZIMMER J KUNZ H
Citation
H. Herzner et al., OLIGOSACCHARIDE SYNTHESIS VIA ELECTROPHILE-INDUCED ACTIVATION OF GLYCOSYL-N-ALLYLCARBAMATES, Journal of carbohydrate chemistry, 17(4-5), 1998, pp. 759-776
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
17
Issue
4-5
Year of publication
1998
Pages
759 - 776
Database
ISI
SICI code
0732-8303(1998)17:4-5<759:OSVEAO>2.0.ZU;2-4
Abstract
Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unpr otected saccharides with allyl isocyanate, can be activated by an elec trophile-induced cyclisation and reacted with glycosyl accepters to fo rm the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild g lycosylation conditions even 1-O-acetyl protected glycosyl accepters c an be used. This was demonstrated in the synthesis of a 1,6-linked glu cosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.