TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

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• Li, T.; Zhang, M.; Lv, P.; Yang, Y.; Schmidt, R. R.; Peng, P. Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2-cis-Xylopyranosylation with O-Xylosyl Imidates as Donors. The Journal of organic chemistry 2023, 89, 804–809. doi:10.1021/acs.joc.3c02339
• Marinus, N.; Eisink, N. N. H. M.; Reintjens, N. R. M.; Dijkstra, R. S.; Havenith, R. W. A.; Minnaard, A. J.; Witte, M. D. A Predictive Model for the Pd-Catalyzed Site-Selective Oxidation of Diols. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202300318. doi:10.1002/chem.202300318
• Carlier, M.; Poisson, T.; Mollet, J.-C.; Lerouge, P.; Sabot, C.; Lehner, A. The Light-Controlled Release of 2-fluoro-l-fucose, an Inhibitor of the Root Cell Elongation, from a nitrobenzyl-caged Derivative. International journal of molecular sciences 2023, 24, 2533. doi:10.3390/ijms24032533
• 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
• Polák, P.; Cossy, J. Ni-Catalyzed Cross-Coupling of 2-Iodoglycals and 2-Iodoribals with Grignard Reagents: A Route to 2-C-Glycosides and 2'-C-Nucleosides. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202104311. doi:10.1002/chem.202104311
• Liu, X.; Lin, Y.; Liu, A.; Sun, Q.; Sun, H.; Xu, P.; Li, G.; Song, Y.; Xie, W.; Sun, H.; Yu, B.; Li, W. 2‐Diphenylphosphinoyl‐acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β‐Glycosides. Chinese Journal of Chemistry 2021, 40, 443–452. doi:10.1002/cjoc.202100865
• Pongener, I.; Pepe, D. A.; Ruddy, J. J.; McGarrigle, E. M. Stereoselective β-mannosylations and β-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide. Chemical science 2021, 12, 10070–10075. doi:10.1039/d1sc01300a
• Ágoston, K.; Watt, G. M. Comprehensive Glycoscience - Methods for O-Glycoside Synthesis. Comprehensive Glycoscience; Elsevier, 2021; pp 103–159. doi:10.1016/b978-0-12-819475-1.00017-1
• Traboni, S.; Bedini, E.; Vessella, G.; Iadonisi, A. Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity. Catalysts 2020, 10, 1142. doi:10.3390/catal10101142
• Chang, C.-W.; Lin, M.-H.; Wu, C.-H.; Chiang, T.-Y.; Wang, C.-C. Mapping Mechanisms in Glycosylation Reactions with Donor Reactivity: Avoiding Generation of Side Products. The Journal of organic chemistry 2020, 85, 15945–15963. doi:10.1021/acs.joc.0c01313
• Kumar, M.; Reddy, T. R.; Gurawa, A.; Kashyap, S. Copper(ii)-catalyzed stereoselective 1,2-addition vs. Ferrier glycosylation of "armed" and "disarmed" glycal donors. Organic & biomolecular chemistry 2020, 18, 4848–4862. doi:10.1039/d0ob01042a
• Tatina, M. B.; Moussa, Z.; Xia, M.; Judeh, Z. M. A. Perfluorophenylboronic acid-catalyzed direct α-stereoselective synthesis of 2-deoxygalactosides from deactivated peracetylated d-galactal. Chemical communications (Cambridge, England) 2019, 55, 12204–12207. doi:10.1039/c9cc06151g
• Kelemen, V.; Bege, M.; Eszenyi, D.; Debreczeni, N.; Bényei, A.; Stürzer, T.; Herczegh, P.; Borbás, A. Stereoselective thioconjugation by photoinduced thiol‐ene coupling reactions of hexo‐ and pentopyranosyl D‐ and L‐glycals at low temperature – Reactivity and stereoselectivity study. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 14555–14571. doi:10.1002/chem.201903095
• Pongener, I.; Nikitin, K.; McGarrigle, E. M. Synthesis of glycosyl chlorides using catalytic Appel conditions. Organic & biomolecular chemistry 2019, 17, 7531–7535. doi:10.1039/c9ob01544b
• Wang, J.; Deng, C.-Q.; Zhang, Q.; Chai, Y. Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Brønsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement. Organic letters 2019, 21, 1103–1107. doi:10.1021/acs.orglett.9b00009
• Yang, G.; Luo, X.; Guo, H.; Wang, Q.; Zhou, J.; Huang, T.; Tang, J.; Shan, J.; Zhang, J. α-Selective synthesis of 2-deoxy-glycosides and disaccharides. Journal of Carbohydrate Chemistry 2018, 37, 128–152. doi:10.1080/07328303.2018.1439498
• Gupta, M. R.; Thakur, K.; Khare, N. K. L-Proline/CeCl3·7H2O-NaI mediated stereoselective synthesis of α-2-deoxy glycosides from glucal. Carbohydrate research 2018, 457, 51–55. doi:10.1016/j.carres.2018.01.003
• Zeng, J.; Xu, Y.; Wang, H.; Meng, L.; Wan, Q. Recent progress on the synthesis of 2-deoxy glycosides. Science China Chemistry 2017, 60, 1162–1179. doi:10.1007/s11426-016-9010-9
• Palo-Nieto, C.; Sau, A.; Williams, R.; Galan, M. C. Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides. The Journal of organic chemistry 2016, 82, 407–414. doi:10.1021/acs.joc.6b02498
• Rasool, F.; Bhat, A. H.; Hussain, N.; Mukherjee, D. Reaction of Glycals with Organic Peroxides: Synthesis of 2-iodo, 2-Deoxy and 2,3-Unsaturated Glycosides. ChemistrySelect 2016, 1, 6553–6557. doi:10.1002/slct.201601849

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