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Stereoselective β‐Mannosylation via Anomeric O‐Alkylation with L‐Sugar‐Derived Electrophiles
dc.contributor.authorHettiarachchi, Ishani Lakshika
dc.contributor.authorMeng, Shuai
dc.contributor.authorChahine, Mira
dc.contributor.authorLi, Xiaohua
dc.contributor.authorZhu, Jianglong
dc.date.accessioned2022-01-06T15:48:18Z
dc.date.available2023-01-06 10:48:16en
dc.date.available2022-01-06T15:48:18Z
dc.date.issued2021-12-28
dc.identifier.citationHettiarachchi, Ishani Lakshika; Meng, Shuai; Chahine, Mira; Li, Xiaohua; Zhu, Jianglong (2021). "Stereoselective β‐Mannosylation via Anomeric O‐Alkylation with L‐Sugar‐Derived Electrophiles." European Journal of Organic Chemistry 2021(48): 6682-6687.
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.urihttps://hdl.handle.net/2027.42/171138
dc.description.abstractA total synthesis of the trisaccharide repeat unit of Salmonella serogroup E1 O‐antigen is reported. This synthesis features a key β‐mannosylation reaction through a cesium carbonate‐mediated anomeric O‐alkylation of a partially protected D‐mannose with an L‐fucose‐derived electrophile for the first time.A total synthesis of the trisaccharide repeat unit of Salmonella serogroup E1 O‐antigen is achieved. The key step involved the Cs2CO3‐mediated anomeric O‐alkylation of partially protected D‐mannose with an L‐fucose‐derived C4‐triflate to furnish desired β‐linked disaccharide in 50 % yield.
dc.publisherWiley Periodicals, Inc.
dc.subject.otherGlycosylation
dc.subject.otherβ-Mannosylation
dc.subject.otherAnomeric O-Alkylation
dc.subject.otherCarbohydrates
dc.subject.otherMicrobial Glycans
dc.titleStereoselective β‐Mannosylation via Anomeric O‐Alkylation with L‐Sugar‐Derived Electrophiles
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/171138/1/ejoc202100903-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/171138/2/ejoc202100903_am.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/171138/3/ejoc202100903.pdf
dc.identifier.doi10.1002/ejoc.202100903
dc.identifier.sourceEuropean Journal of Organic Chemistry
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dc.working.doiNOen
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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