Stereoselective Synthesis of 2-Azido-2-deoxy-β-d-mannosides via Cs2CO3-Mediated Anomeric O-Alkylation with Primary Triflates: Synthesis of a Tetrasaccharide Fragment of Micrococcus luteus Teichuronic Acid
Author:
Affiliation:
1. Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States
Funder
University of Toledo
National Institute of General Medical Sciences
Publisher
American Chemical Society (ACS)
Subject
Organic Chemistry
Link
https://pubs.acs.org/doi/pdf/10.1021/acs.joc.0c02370
Reference44 articles.
1. Recent advances in the construction of β-D-mannose and β-D-mannosamine linkages
2. Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry
3. 1,2-cis O-Glycosylation: Methods, Strategies, Principles
4. Boronic-Acid-Catalyzed Regioselective and 1,2-cis-Stereoselective Glycosylation of Unprotected Sugar Acceptors via SNi-Type Mechanism
5. Recent topics in β-stereoselective mannosylation
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1. Dynamic Kinetic Stereoselective Glycosylation via RhII and Chiral Phosphoric Acid‐Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates;Angewandte Chemie International Edition;2023-08-21
2. Dynamic Kinetic Stereoselective Glycosylation via RhII and Chiral Phosphoric Acid‐Cocatalyzed Carbenoid Insertion to the Anomeric OH Bond for the Synthesis of Glycoconjugates;Angewandte Chemie;2023-08-21
3. Potassium carbonate-mediated β-selective anomeric O-alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids;Tetrahedron Letters;2023-06
4. Synthesis of 2-Amino-2-deoxy-β-d-mannosides via Stereoselective Anomeric O-Alkylation of 2N,3O-Oxazolidinone-Protected d-Mannosamine: Synthesis of the Trisaccharide Repeating Unit of Streptococcus pneumoniae 19F Polysaccharide;Organic Letters;2023-05-31
5. Stereoselective Synthesis of β-d-Manno-heptopyranoside via Cs2CO3-Mediated Anomeric O-Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Bacillus thermoaerophilus Surface-Layer Glycoprotein;The Journal of Organic Chemistry;2022-05-10
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