Hydrogen-bond-mediated aglycone delivery (HAD): a highly stereoselective synthesis of 1,2-cis α-D-glucosides from common glycosyl donors in the presence of bromine

Chemistry : a European Journal
Jagodige P Yasomanee, Alexei V Demchenko

Abstract

Described herein is the expansion of the picoloyl protecting-group assisted H-bond mediated aglycone delivery (HAD) method recently introduced by our laboratory. At first it was noticed that high α-stereoselectivity is only obtained with S-ethyl glycosyl donors and only in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), in high dilution, and low temperature. Combining the mechanistic studies of the HAD reaction and bromine-promoted glycosylations allowed a very effective method to be devised that allows for highly stereoselective α-glycosidation of practically all common leaving groups (S-phenyl, S-tolyl, S/O-imidates) at regular concentrations and ambient temperature.

References

Jun 10, 2004·Angewandte Chemie·Alexei V DemchenkoNelli N Malysheva
Aug 7, 2007·The Journal of Organic Chemistry·Medha N KamatAlexei V Demchenko
Aug 7, 2007·The Journal of Organic Chemistry·Medha N KamatAlexei V Demchenko
Nov 20, 2010·Organic Letters·Sneha C RanadeAlexei V Demchenko
May 14, 2011·Organic Letters·Laurel K MydockAlexei V Demchenko
Dec 6, 2011·The Journal of Organic Chemistry·Sophon KaeothipAlexei V Demchenko
Nov 22, 2012·Journal of the American Chemical Society·Jagodige P Yasomanee, Alexei V Demchenko
Apr 1, 2012·Chemistry of Heterocyclic Compounds·S J Hasty, A V Demchenko
Jan 30, 2014·Organic Letters·Salvatore G PistorioAlexei V Demchenko
Aug 15, 2014·Angewandte Chemie·Jagodige P Yasomanee, Alexei V Demchenko

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Citations

Jan 20, 2016·Journal of the American Chemical Society·Peng-Cheng GaoJin-Song Yang
Sep 10, 2015·Organic Letters·Abhijeet K KayasthaAlexei V Demchenko
Feb 26, 2016·Organic & Biomolecular Chemistry·Jagodige P YasomaneeAlexei V Demchenko
Oct 25, 2017·Beilstein Journal of Organic Chemistry·Xiao G Jia, Alexei V Demchenko
Jul 2, 2020·Organic & Biomolecular Chemistry·Scott A GeringerAlexei V Demchenko
Oct 27, 2020·The Journal of Organic Chemistry·Robin A JeanneretM Carmen Galan
Jul 23, 2021·The Journal of Organic Chemistry·Deqin CaiKan Ding
Apr 30, 2017·Organic Letters·Samira EscopyCristina De Meo
Jun 29, 2018·Chemical Reviews·Matteo PanzaAlexei V Demchenko
Aug 20, 2021·Organic Letters·Siai ZhouFeiqing Ding
Feb 5, 2019·Journal of the American Chemical Society·Larissa Krasnova, Chi-Huey Wong
Nov 14, 2019·The Journal of Organic Chemistry·Bradley JonesCristina De Meo
May 9, 2019·The Journal of Organic Chemistry·Salvatore G PistorioAlexei V Demchenko

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