0000000000131813

AUTHOR

Jörg Zimmer

showing 5 related works from this author

ChemInform Abstract: Glycoside Synthesis via Electrophile-Induced Activation of N-Allyl Carbamates.

2010

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.

chemistry.chemical_classificationStereochemistryorganic chemicalsGlycosideGeneral MedicineGlycoside synthesischemistry.chemical_compoundchemistryElectrophileMonosaccharideOrganic chemistrylipids (amino acids peptides and proteins)GlycosylAllyl isocyanateChemInform
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ChemInform Abstract: Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-allylcarbamates.

2010

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.

chemistry.chemical_classificationanimal structuresGlycosylationStereochemistryMucinfood and beveragesmacromolecular substancesGeneral Medicinecarbohydrates (lipids)chemistry.chemical_compoundchemistryElectrophilelipids (amino acids peptides and proteins)GlycosylTrisaccharideAllyl isocyanateOligosaccharide synthesisChemInform
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Stereoselective Synthesis of β-1-O-Acyl Derivatives of Carbohydrates: An Application of the Cesium Effect.

1992

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.

chemistry.chemical_classificationStereochemistryOrganic Chemistrychemistry.chemical_elementBiochemistryAcylationchemistry.chemical_compoundAldosechemistryCaesiumDrug DiscoverySN2 reactionOrganic chemistrylipids (amino acids peptides and proteins)StereoselectivityCarboxylateTetrahedron Letters
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ChemInform Abstract: Stereoselective Synthesis of β-1-O-Acyl Derivatives of Carbohydrates: An Application of the Cesium Effect.

2010

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.

chemistryCaesiumOrganic chemistrychemistry.chemical_elementlipids (amino acids peptides and proteins)StereoselectivityGeneral MedicineChemInform
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Glycoside synthesis via electrophile-induced activation of N-allyl carbamates

1993

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.

chemistry.chemical_classificationDipeptideorganic chemicalsOrganic ChemistryDisaccharideGlycosideBiochemistryMedicinal chemistrychemistry.chemical_compoundchemistryAldoseDrug DiscoveryElectrophileMonosaccharidelipids (amino acids peptides and proteins)GlycosylStereoselectivityTetrahedron Letters
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