0000000000131813
AUTHOR
Jörg Zimmer
ChemInform Abstract: Glycoside Synthesis via Electrophile-Induced Activation of N-Allyl Carbamates.
Abstract O-Benzyl-, O-acyl-, N-acyl- and isopropylidene-protected glycosyl N-allylcarbamates, obtained from anomerically unprotected monosaccharides and allyl isocyanate, are activated by an electrophile-induced cyclisation and react with hydroxyl compounds to form the corresponding glycosides.
ChemInform Abstract: Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-allylcarbamates.
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.
Stereoselective Synthesis of β-1-O-Acyl Derivatives of Carbohydrates: An Application of the Cesium Effect.
Abstract The stereoselective formation of anomerically pure 1-O-acyl derivatives of protected carbohydrates is achieved by reaction of the α-glycosyl halogenoses with cesium caboxylates.
ChemInform Abstract: Stereoselective Synthesis of β-1-O-Acyl Derivatives of Carbohydrates: An Application of the Cesium Effect.
Abstract The stereoselective formation of anomerically pure 1-O-acyl derivatives of protected carbohydrates is achieved by reaction of the α-glycosyl halogenoses with cesium caboxylates.
Glycoside synthesis via electrophile-induced activation of N-allyl carbamates
Abstract O-Benzyl-, O-acyl-, N-acyl- and isopropylidene-protected glycosyl N-allylcarbamates, obtained from anomerically unprotected monosaccharides and allyl isocyanate, are activated by an electrophile-induced cyclisation and react with hydroxyl compounds to form the corresponding glycosides.