On the nitrile effect in L-rhamnopyranosylation.

Carbohydrate Research
David Crich, Mitesh Patel

Abstract

It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the beta-selectivity of a number of L-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride couple. The use of more significant quantities of acetonitrile or propionitrile results in the formation of complex reaction mixtures containing little coupled product, but from which Ritter-type products can be isolated.

References

Feb 15, 2002·Carbohydrate Research·Adel A-H Abdel-RahmanRichard R Schmidt
Aug 16, 2002·Combinatorial Chemistry & High Throughput Screening·Anders LohseOle Hindsgaul
Dec 31, 2002·Carbohydrate Research·Michael RammMatthias Hamburger
Feb 28, 2003·Organic Letters·David Crich, John Picione
Apr 26, 2003·Organic Letters·Jeroen D C CodéeGijs A van der Marel
Dec 4, 1998·Angewandte Chemie·Thomas Ziegler, Gregor Lemanski

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Citations

May 26, 2016·The Journal of Organic Chemistry·Mads HeuckendorffHenrik H Jensen
Nov 21, 2007·Organic & Biomolecular Chemistry·Vanessa Leiria CampoRobert A Field
Jan 7, 2016·Beilstein Journal of Organic Chemistry·Madhuri Vangala, Ganesh P Shinde
Apr 10, 2020·Organic & Biomolecular Chemistry·Diksha Rai, Suvarn S Kulkarni
May 29, 2018·European Journal of Organic Chemistry·Bo YangXuefei Huang
Sep 15, 2011·Chemistry : a European Journal·Chin-Sheng ChaoKwok-kong Tony Mong
Jan 24, 2009·The Journal of Organic Chemistry·Enoch A MensahHien M Nguyen
Apr 30, 2015·Chemical Reviews·Tobias Gylling FrihedChristian Marcus Pedersen
Aug 19, 2007·Journal of the American Chemical Society·Toshiki NokamiJun-ichi Yoshida

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