Silyl-protective groups influencing the reactivity and selectivity in glycosylations

Scholarly Works

• Zeng, C.; Zhang, H.; Zhu, D.; Yu, B. Convergent Synthesis of the Nonreducing Hexasaccharide Fragment and the Dodecasaccharide Scaffold of Marine Lipopolysaccharide Axinelloside A. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, e202400075. doi:10.1002/chem.202400075
• Vašíček, T.; Arensmeyer, B.; Monti, A.; Zamyatina, A. Versatile approach towards fully desymmetrized trehalose with a novel set of orthogonal protecting groups. Frontiers in chemistry 2024, 11, 1332837. doi:10.3389/fchem.2023.1332837
• Golubev, A. V.; Kubasov, A. S.; Lukoshkova, A. A.; Sarkisov, N. A.; Novikov, I. V.; Starodubets, P. A.; Bykov, A. Y.; Zhdanov, A. P.; Zhizhin, K. Y.; Kuznetsov, N. T. Synthesis of New Iminium Derivatives of Sulphonio-сloso-Decaborate Anion (Bu4N)[2-B10H9SC(NH2)R] (R = –CH3, –CH2CH3, –CH(CH3)2, –Ph, –PhCH3). Russian Journal of Inorganic Chemistry 2023, 68, 1752–1760. doi:10.1134/s0036023623602350
• Karpenko, M. Y.; Abronina, P. I.; Zinin, A. I.; Chizhov, A. O.; Kononov, L. O. TIPS group-assisted isomerization of benzyl protected d-manno- and d-glucopyranose to d-fructofuranose derivatives. Carbohydrate research 2023, 534, 108942. doi:10.1016/j.carres.2023.108942
• Liu, H.; Lang, M.; Hazelard, D.; Compain, P. A Fries-Type Rearrangement Strategy for the Construction of Stereodefined Quaternary Pseudoanomeric Centers: An Entry into C-Naphthyl Ketosides. The Journal of organic chemistry 2023, 88, 13847–13856. doi:10.1021/acs.joc.3c01474
• Ramazanova, K.; Chakrabortty, S.; Kallmeier, F.; Kretzschmar, N.; Tin, S.; Lönnecke, P.; de Vries, J. G.; Hey-Hawkins, E. Access to Enantiomerically Pure P-Chiral 1-Phosphanorbornane Silyl Ethers. Molecules (Basel, Switzerland) 2023, 28, 6210. doi:10.3390/molecules28176210
• Asano, T.; Udagawa, T.; Komura, N.; Imamura, A.; Ishida, H.; Ando, H.; Tanaka, H.-N. Unprecedented neighboring group participation of C2 N-imidoxy functionalities for 1,2-trans-selective glycosylation. Carbohydrate research 2023, 527, 108808. doi:10.1016/j.carres.2023.108808
• Rahaman Molla, M.; Thakur, R.; Aghi, A.; Kumar, A. C2‐Cyanomethyl (CNMe) Ether‐Protected Glycosyl Trichloroacetimidate Donors for Stereoselective β‐O‐Glycosylations. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202300079
• Majik, M. S.; Ghare, V. M. Green nanoparticles for protection and deprotection reactions in organic synthesis. Nanoparticles in Green Organic Synthesis; Elsevier, 2023; pp 173–193. doi:10.1016/b978-0-323-95921-6.00001-9
• Mukherji, A.; Rotta, M. K. V.; Sarmah, B. K.; Kancharla, P. K. Influence of Various Silyl Protecting Groups on Stereoselective 2-Deoxyrhamnosylation. The Journal of organic chemistry 2022, 88, 245–260. doi:10.1021/acs.joc.2c02285
• Howell, L. W.; Friestad, G. K. On the role of β-silyloxy- and β-alkoxyaldehyde protecting groups in Mukaiyama aldol 1,3-diastereocontrol. Tetrahedron Letters 2022, 111, 154203. doi:10.1016/j.tetlet.2022.154203
• Li, S.-J.; Fang, Q.; Huang, Y.-W.; Luo, Y.-Y.; Mu, X.-D.; Li, L.; Yin, X.-C.; Yang, J.-S. Chemical Synthesis of the Nonreducing Hexasaccharide Fragment of Axinelloside A Based on a Stepwise Glycosylation Approach. Organic letters 2022, 24, 7088–7094. doi:10.1021/acs.orglett.2c02618
• Cloutier, M.; Lavoie, S.; Gauthier, C. C7 Epimerization of Benzylidene-Protected β-d-Idopyranosides Brings Structural Insights into Idose Conformational Flexibility. The Journal of organic chemistry 2022, 87, 12932–12953. doi:10.1021/acs.joc.2c01504
• Ghosh, T.; Nokami, T. Recent development of stereoselective C-glycosylation via generation of glycosyl radical. Carbohydrate research 2022, 522, 108677. doi:10.1016/j.carres.2022.108677
• Liu, H.; Laporte, A. G.; Tardieu, D.; Hazelard, D.; Compain, P. Formal Glycosylation of Quinones with exo-Glycals Enabled by Iron-Mediated Oxidative Radical-Polar Crossover. The Journal of organic chemistry 2022, 87, 13178–13194. doi:10.1021/acs.joc.2c01635
• Reisenbauer, J. C.; Green, O.; Franchino, A.; Finkelstein, P.; Morandi, B. Late-stage diversification of indole skeletons through nitrogen atom insertion. Science (New York, N.Y.) 2022, 377, 1104–1109. doi:10.1126/science.add1383
• Abronina, P. I.; Malysheva, N. N.; Zinin, A. I.; Kolotyrkina, N. G.; Kononov, L. O. Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202200517
• Kuciński, K.; Stachowiak-Dłużyńska, H.; Hreczycho, G. Catalytic silylation of O–nucleophiles via Si–H or Si–C bond cleavage: A route to silyl ethers, silanols and siloxanes. Coordination Chemistry Reviews 2022, 459, 214456. doi:10.1016/j.ccr.2022.214456
• König, H. F.; Rummel, L.; Hausmann, H.; Becker, J.; Schümann, J. M.; Schreiner, P. R. Gauging the Steric Effects of Silyl Groups with a Molecular Balance. The Journal of organic chemistry 2022, 87, 4670–4679. doi:10.1021/acs.joc.1c03103
• Abronina, P. I.; Podvalnyy, N. M.; Kononov, L. O. The use of silyl groups in the synthesis of arabinofuranosides. Russian Chemical Bulletin 2022, 71, 6–29. doi:10.1007/s11172-022-3371-z

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