The Journal of organic chemistry

SnCl4-and TiCl4-catalyzed anomerization of acylated O-and S-glycosides: analysis of factors that lead to higher α: β anomer ratios and reaction rates

W Pilgrim, PV Murphy

Index: Pilgrim, Wayne; Murphy, Paul V. Journal of Organic Chemistry, 2010 , vol. 75, # 20 p. 6747 - 6755

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Citation Number: 41

Abstract

The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl4 and TiCl4 and how this has informed the synthesis of α-O-and α-S-glycolipids is discussed. The SnCl4-catalyzed anomerization reactions of β-S-and β-O- glycosides of 18 substrates followed first order equilibrium kinetics and kf+ kr values were obtained, where kf is the rate constant for the forward reaction (β→ α) and kr is the rate ...

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