Benzyne arylation of oxathiane glycosyl donors

Scholarly Works

• Duong, T.; Valenzuela, E. A.; Ragains, J. R. Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors. Organic letters 2023, 25, 8526–8529. doi:10.1021/acs.orglett.3c03502
• Kumar, M.; Kumar, N.; Gurawa, A.; Kashyap, S. Protecting group enabled stereocontrolled approach for rare-sugars talose/gulose via dual-ruthenium catalysis. Carbohydrate research 2022, 523, 108705. doi:10.1016/j.carres.2022.108705
• Ikawa, T. Simple arylation. Comprehensive Aryne Synthetic Chemistry; Elsevier, 2022; pp 15–56. doi:10.1016/b978-0-323-85153-4.00003-4
• Tokatly, A. I.; Vinnitskiy, D. Z.; Ustuzhanina, N. E.; Nifantiev, N. E. Protecting Groups as a Factor of Stereocontrol in Glycosylation Reactions. Russian Journal of Bioorganic Chemistry 2021, 47, 53–70. doi:10.1134/s1068162021010258
• Takahashi, D.; Toshima, K. Comprehensive Glycoscience - 1,2-cis O-Glycosylation Methods. Comprehensive Glycoscience; Elsevier, 2021; pp 365–412. doi:10.1016/b978-0-12-819475-1.00016-x
• Khanam, A.; Tiwari, A.; Mandal, P. K. Chiral auxiliaries: Usefullness in stereoselective glycosylation reactions and their synthetic applications. Carbohydrate research 2020, 495, 108045. doi:10.1016/j.carres.2020.108045
• Marianski, M.; Mucha, E.; Greis, K.; Moon, S.; Pardo, A.; Kirschbaum, C.; Thomas, D. A.; Meijer, G.; von Helden, G.; Gilmore, K.; Seeberger, P. H.; Pagel, K. Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy. Angewandte Chemie (International ed. in English) 2020, 59, 6166–6171. doi:10.1002/anie.201916245
• Marianski, M.; Mucha, E.; Greis, K.; Moon, S.; Pardo, A.; Kirschbaum, C.; Thomas, D. A.; Meijer, G.; von Helden, G.; Gilmore, K.; Seeberger, P. H.; Pagel, K. Direct Evidence for Remote Participation in Galactose Building Blocks during Glycosylations Revealed by Cryogenic Vibrational Spectroscopy. Angewandte Chemie 2020, 132, 6224–6229. doi:10.1002/ange.201916245
• Zeng, J.; Liu, Y.; Chen, W.; Zhao, X.; Meng, L.; Wan, Q. Glycosyl Sulfoxides in Glycosylation Reactions. Topics in current chemistry (Cham) 2018, 376, 27. doi:10.1007/s41061-018-0205-4
• Mensink, R. A.; Boltje, T. J. Advances in Stereoselective 1,2-cis Glycosylation using C-2 Auxiliaries. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 17637–17653. doi:10.1002/chem.201700908
• Whitfield, D. M.; Guo, J. Proton transfer and hydrogen bonding in glycosylation reactions. Journal of Carbohydrate Chemistry 2017, 36, 59–99. doi:10.1080/07328303.2017.1365369
• Boltje, T. J.; Liu, L.; Boons, G.-J. Glycochemical Synthesis; Wiley, 2016; pp 97–129. doi:10.1002/9781119006435.ch4
• Huang, W.; Gao, Q.; Boons, G.-J. Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 12920–12926. doi:10.1002/chem.201501844
• Laezza, A.; De Castro, C.; Parrilli, M.; Bedini, E. Inter vs. intraglycosidic acetal linkages control sulfation pattern in semi-synthetic chondroitin sulfate. Carbohydrate polymers 2014, 112, 546–555. doi:10.1016/j.carbpol.2014.05.085
• Yang, L.; Qin, Q.; Ye, X.-S. Preactivation: An Alternative Strategy in Stereoselective Glycosylation and Oligosaccharide Synthesis. Asian Journal of Organic Chemistry 2013, 2, 30–49. doi:10.1002/ajoc.201200136
• Fang, T.; Mo, K.-F.; Boons, G.-J. Stereoselective assembly of complex oligosaccharides using anomeric sulfonium ions as glycosyl donors. Journal of the American Chemical Society 2012, 134, 7545–7552. doi:10.1021/ja3018187
• Lindhorst, T. K. Synthesis in the glycosciences II. Beilstein journal of organic chemistry 2012, 8, 411–412. doi:10.3762/bjoc.8.45
• Rijs, N. J.; O'Hair, R. A. J. Forming trifluoromethylmetallates: competition between decarboxylation and C-F bond activation of group 11 trifluoroacetate complexes, [CF3CO2ML]-. Dalton transactions (Cambridge, England : 2003) 2012, 41, 3395–3406. doi:10.1039/c2dt12117d
• Fascione, M. A.; Adshead, S. J.; Mandal, P. K.; Kilner, C. A.; Leach, A. G.; Turnbull, W. B. Mechanistic Studies on a Sulfoxide Transfer Reaction Mediated by Diphenyl Sulfoxide/Triflic Anhydride. Chemistry (Weinheim an der Bergstrasse, Germany) 2012, 18, 2987–2997. doi:10.1002/chem.201102861
• Fascione, M. A.; Kilner, C. A.; Leach, A. G.; Turnbull, W. B. Do Glycosyl Sulfonium Ions Engage in Neighbouring‐Group Participation? A Study of Oxathiane Glycosyl Donors and the Basis for their Stereoselectivity. Chemistry (Weinheim an der Bergstrasse, Germany) 2011, 18, 321–333. doi:10.1002/chem.201101889

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