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Stereoselective Construction of β‐Mannopyranosides by Anomeric O‐Alkylation: Synthesis of the Trisaccharide Core of N‐linked Glycans

dc.contributor.authorNguyen, Hai
dc.contributor.authorZhu, Danyang
dc.contributor.authorLi, Xiaohua
dc.contributor.authorZhu, Jianglong
dc.date.accessioned2017-06-16T20:16:38Z
dc.date.available2017-06-16T20:16:38Z
dc.date.issued2016-04-04
dc.identifier.citationNguyen, Hai; Zhu, Danyang; Li, Xiaohua; Zhu, Jianglong (2016). "Stereoselective Construction of β‐Mannopyranosides by Anomeric O‐Alkylation: Synthesis of the Trisaccharide Core of N‐linked Glycans." Angewandte Chemie 128(15): 4845-4849.
dc.identifier.issn0044-8249
dc.identifier.issn1521-3757
dc.identifier.urihttps://hdl.handle.net/2027.42/137600
dc.description.abstractA new and efficient approach for direct and stereoselective synthesis of β‐mannopyranosides by anomeric O‐alkylation has been developed. This anomeric O‐alkylation of mannopyranose‐derived lactols is proposed to occur under synergistic control of a kinetic anomeric effect and metal chelation. The presence of a conformationally flexible C6 oxygen atom in the sugar‐derived lactol donors is required for this anomeric O‐alkylation to be efficient, probably because of its chelation with cesium ion. In contrast, the presence of a C2 oxygen atom plays a minor role. This glycosylation method has been successfully utilized for the synthesis of the trisaccharide core of complex N‐linked glycans.Lactol‐Kontrolle: Die Titelreaktion könnte synergistisch durch einen kinetischen anomeren Effekt und Metallchelatisierung gesteuert ablaufen. Nur mit einem an der C6‐Position des Lactols befindlichen, konformativ flexiblen Sauerstoffatom, das vermutlich chelatisierend an ein Caesiumion bindet, ist die Reaktion effizient. Diese Glykosylierungsmethode bewährte sich in der Synthese der Trisaccharid‐Kerns komplexer N‐verknüpfter Glykane.
dc.publisherOxford University Press
dc.publisherWiley Periodicals, Inc.
dc.subject.otherβ-Mannosylierungen
dc.subject.otherOligosaccharide
dc.subject.otherN-verknüpfte Glykane
dc.subject.otherGlykosylierungen
dc.subject.otherAnomere O-Alkylierung
dc.titleStereoselective Construction of β‐Mannopyranosides by Anomeric O‐Alkylation: Synthesis of the Trisaccharide Core of N‐linked Glycans
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137600/1/ange201600488_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137600/2/ange201600488-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137600/3/ange201600488.pdf
dc.identifier.doi10.1002/ange.201600488
dc.identifier.sourceAngewandte Chemie
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