β-Mannosylation of N-acetyl glucosamine by propargyl mediated intramolecular aglycon delivery (IAD): synthesis of the N-glycan core pentasaccharide |
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Authors: | Emanuele Attolino |
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Institution: | Chemistry Research Laboratory, Oxford University, Mansfield Road, Oxford OX1 3TA, UK |
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Abstract: | An efficient and completely stereocontrolled synthesis of the N-glycan Manβ(1-4)GlcNAc disaccharide is achieved by propargyl mediated intramolecular aglycon delivery (IAD). Isomerisation of the 2-O-progargyl group of a manno thioglycoside to an allene is followed by iodonium ion mediated mixed acetal formation with the 4-OH of a protected GlcNAc derivative, and subsequent intramolecular glycosylation with complete control of anomeric stereochemistry. Access to this key disaccharide intermediate allows completion of the total synthesis of the core N-glycan pentasaccharide. |
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Keywords: | Carbohydrates Glycosylation Intramolecular aglycon delivery β-Mannosides N-Glycan Pentasaccharide |
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