A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Chemistry : a European Journal
Scott A GeringerAlexei V Demchenko

Abstract

Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides have been successfully glycosidated, and these reaction conditions proved to be effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of the reaction can be monitored visually; its completion can be judged by the disappearance of the characteristic dark color of Ag2 O.

References

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Sep 30, 2004·Angewandte Chemie·Xuefei HuangXin-Shan Ye
Oct 11, 2005·Carbohydrate Research·K Jayakanthan, Yashwant D Vankar
Jul 27, 2006·Journal of the American Chemical Society·Srinivas Hotha, Sudhir Kashyap
Aug 31, 2006·Journal of the American Chemical Society·Zhitao Li, Jeffrey C Gildersleeve
Nov 28, 2006·Carbohydrate Research·Aileen F G Bongat, Alexei V Demchenko
Mar 21, 2008·Journal of Combinatorial Chemistry·Lourdes Encinas, Jose Luis Chiara
May 3, 2008·Carbohydrate Research·Cristina De Meo, Uvege Priyadarshani
Jun 9, 2009·Advances in Carbohydrate Chemistry and Biochemistry·James T Smoot, Alexei V Demchenko
Nov 20, 2010·Organic Letters·Sneha C RanadeAlexei V Demchenko
Jun 15, 2011·Carbohydrate Research·Sophon Kaeothip, Alexei V Demchenko
May 9, 2012·Beilstein Journal of Organic Chemistry·Hemali D Premathilake, Alexei V Demchenko
May 16, 2013·Organic & Biomolecular Chemistry·Swati S NigudkarAlexei V Demchenko
Jun 1, 2016·Angewandte Chemie·Lifeng SunXin-Shan Ye
Jan 14, 2017·Science·Yongho ParkEric N Jacobsen
Dec 12, 2017·The Journal of Organic Chemistry·Yashapal SinghAlexei V Demchenko
Nov 9, 2018·Chemistry : a European Journal·Yashapal Singh, Alexei V Demchenko
Nov 16, 2018·Organic & Biomolecular Chemistry·Scott A Geringer, Alexei V Demchenko
Dec 5, 2018·Advances in Carbohydrate Chemistry and Biochemistry·Cristina De Meo, Bradley T Jones
Oct 16, 2019·Chemistry : a European Journal·Yashapal Singh, Alexei V Demchenko

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Citations

Apr 23, 2021·Organic & Biomolecular Chemistry·Hayley B SteberAlexei V Demchenko
Jul 17, 2021·Organic Letters·Mei-Huei LinCheng-Chung Wang
Jul 7, 2020·The Journal of Organic Chemistry·Ganesh ShresthaAlexei V Demchenko

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