α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

The Journal of Organic Chemistry
Sam J MoonsThomas J Boltje

Abstract

Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.

References

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Aug 25, 2005·Journal of the American Chemical Society·Jin-Hwan KimGeert-Jan Boons
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Feb 18, 2010·Nature Chemistry·Thomas J BoltjeGeert-Jan Boons
Dec 17, 2010·Organic Letters·Thomas J BoltjeGeert-Jan Boons
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May 14, 2011·Organic Letters·Laurel K MydockAlexei V Demchenko
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May 26, 2016·The Journal of Organic Chemistry·Mads HeuckendorffHenrik H Jensen
Jul 26, 2017·Chemistry : a European Journal·Rens A Mensink, Thomas J Boltje

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Citations

Sep 19, 2019·Chemical Communications : Chem Comm·Ze-Yu Tian, Cheng-Pan Zhang
Jan 3, 2020·Chemistry, an Asian Journal·Bhaswati Ghosh, Suvarn S Kulkarni
Jan 28, 2020·Organic & Biomolecular Chemistry·Frank F J de KleijneThomas J Boltje
Mar 21, 2020·Organic & Biomolecular Chemistry·Dancan K NjeriJustin R Ragains
Feb 19, 2020·The Journal of Organic Chemistry·Jean-François ParentPierre Deslongchamps

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Methods Mentioned

BETA
glycosylations
glycosylation
NMR
column chromatography
column

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