2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis.

Beilstein Journal of Organic Chemistry
Hemali D Premathilake, Alexei V Demchenko

Abstract

The O-allylphenyl (AP) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of efficient oligosaccharide assembly.

References

Jun 10, 2004·Angewandte Chemie·Alexei V DemchenkoNelli N Malysheva
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Sep 30, 2004·Angewandte Chemie·Xuefei HuangXin-Shan Ye
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Jun 9, 2009·Advances in Carbohydrate Chemistry and Biochemistry·James T Smoot, Alexei V Demchenko
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Nov 20, 2010·Organic Letters·Sneha C RanadeAlexei V Demchenko
Dec 2, 2010·Topics in Current Chemistry·Hemali D Premathilake, Alexei V Demchenko
Jun 15, 2011·Carbohydrate Research·Sophon Kaeothip, Alexei V Demchenko
Mar 1, 2012·Carbohydrate Research·Shun-Yuan LuoShang-Cheng Hung

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Citations

Jul 22, 2014·Carbohydrate Research·Sneha C Ranade, Alexei V Demchenko
Apr 27, 2016·Organic Letters·Papapida PornsuriyasakAlexei V Demchenko
Nov 11, 2014·Beilstein Journal of Organic Chemistry·Thisbe K Lindhorst
Mar 8, 2020·Chemistry : a European Journal·Scott A GeringerAlexei V Demchenko
Feb 19, 2021·Organic & Biomolecular Chemistry·Samira EscopyAlexei V Demchenko
Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung

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Methods Mentioned

BETA
glycosylation
glycosylations
silica gel column chromatography

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