Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Scholarly Works

• Bouché, L.; Zimmer, R.; Reissig, H. Multivalent Aminoseptanose Mimetics by Copper‐Catalyzed (3+2) Cycloadditions of Azidomethyl‐Substituted Bicyclic 1,2‐Oxazines. European Journal of Organic Chemistry 2024, 27. doi:10.1002/ejoc.202301294
• Reissig, H.-U.; Koóš, P. Synthesis of Novel Enantiopure Amino- and Azidopyran Building Blocks and Their Click Reactions to Multivalent Carbohydrate Mimetics. Synthesis 2023, 56, 795–808. doi:10.1055/s-0043-1763619
• Majireck, M. M.; Bennett, J. M. Comprehensive Heterocyclic Chemistry IV - 1,2-Oxazines and Their Benzo Derivatives. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 283–415. doi:10.1016/b978-0-12-818655-8.00013-5
• Salta, J.; Arp, F. F.; Kühne, C.; Reissig, H.-U. Multivalent 1,2,3-Triazole-Linked Carbohydrate Mimetics by Huisgen–Meldal-Sharpless Cycloadditions of an Azidopyran. European Journal of Organic Chemistry 2020, 2020, 7333–7342. doi:10.1002/ejoc.202001389
• Salta, J.; Reissig, H.-U. Divalent Triazole‐Linked Carbohydrate Mimetics: Synthesis by Click Chemistry and Evaluation as Selectin Ligands. European Journal of Organic Chemistry 2020, 2020, 4361–4370. doi:10.1002/ejoc.202000618
• Tavernaro, I.; Rodrigo, A. M.; Kandziora, M.; Kuntz, S.; Dernedde, J.; Trautwein, C.; Tacke, F.; Blas‐Garcia, A.; Bartneck, M. Modulating Myeloid Immune Cell Migration Using Multivalently Presented Monosaccharide Ligands for Advanced Immunotherapy. Advanced Therapeutics 2019, 2, 1900145. doi:10.1002/adtp.201900145
• Adam, L.; Schefzig, L.; Pecchioli, T.; Zimmer, R.; Reissig, H.-U. New bifunctional carbohydrate-like thiourea derivatives – design and first application in organocatalysis. Synthetic Communications 2018, 48, 1945–1956. doi:10.1080/00397911.2018.1468465
• Medvecký, M.; Linder, I.; Schefzig, L.; Reissig, H.-U.; Zimmer, R. Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions. Beilstein journal of organic chemistry 2016, 12, 2898–2905. doi:10.3762/bjoc.12.289
• Salta, J.; Dernedde, J.; Reissig, H.-U. Synthesis of multivalent carbohydrate mimetics with aminopolyol end groups and their evaluation as L-selectin inhibitors. Beilstein journal of organic chemistry 2015, 11, 638–646. doi:10.3762/bjoc.11.72
• Kandziora, M.; Reissig, H.-U. Preparation of Multivalent Carbohydrate Mimetics Based on Enantiopure 1,2‐Oxazines by Sonogashira Coupling and Subsequent Reductive Ring‐Opening. European Journal of Organic Chemistry 2014, 2015, 370–377. doi:10.1002/ejoc.201403186
• Kandziora, M.; Reissig, H.-U. Synthesis of rigid p-terphenyl-linked carbohydrate mimetics. Beilstein journal of organic chemistry 2014, 10, 1749–1758. doi:10.3762/bjoc.10.182
• Jasiński, M.; Mlostoń, G.; Stolarski, M.; Costa, W.; Domínguez, M.; Reissig, H.-U. Reactions of Cycloaliphatic Thioketones and Their Oxo Analogues with Lithiated Methoxyallene: A New Approach to Vinylthiiranes. Chemistry, an Asian journal 2014, 9, 2641–2648. doi:10.1002/asia.201402547
• Bouché, L.; Reissig, H.-U. Synthesis of Di‐ and Trivalent Carbohydrate Mimetics with Oxepane Substructure by Employing Copper‐Catalyzed [3+2] Cycloadditions of Alkynes with Azido­oxepanes. European Journal of Organic Chemistry 2014, 2014, 3697–3703. doi:10.1002/ejoc.201402191

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