6533b7d3fe1ef96bd1261293

RESEARCH PRODUCT

ChemInform Abstract: Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-allylcarbamates.

Holger HerznerHorst KunzJörg ZimmerJörg EberlingM. Schultz

subject

chemistry.chemical_classificationanimal structuresGlycosylationStereochemistryMucinfood and beveragesmacromolecular substancesGeneral Medicinecarbohydrates (lipids)chemistry.chemical_compoundchemistryElectrophilelipids (amino acids peptides and proteins)GlycosylTrisaccharideAllyl isocyanateOligosaccharide synthesis

description

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. 1. Dedicated to the memory of Professor Akira Hasegawa.

yearjournalcountryeditionlanguage
2010-06-18ChemInform
https://doi.org/10.1002/chin.199849252