Catalytic Appel Synthesis of Glycosyl Chlorides

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1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

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Catalytic Appel Synthesis of Glycosyl Chlorides

Imlirenla Pongener 1 , Kirill Nikitin 1 , Eoghan M. McGarrigle 1

1 Centre for Synthesis and Chemical Biology, School of Chemistry, University College Dublin, Dublin, Ireland

Glycosyl chlorides are useful donors and precursors in oligosaccharide synthesis. Commonly used methods for synthesis of glycosyl chlorides from hemiacetals require stoichiometric amounts of reagents, additional additives or heating.[1,2] Herein, we report a new method to synthesise glycosyl chlorides using catalytic Appel conditions.[3,4] Triphenylphosphine oxide, which is generally a stoichiometric waste product in conventional Appel reactions, is used as a catalyst in our method (Scheme 1).

We will also describe our efforts to develop a one-pot glycosylation via the interception of the alkoxyphosphonium intermediate.

Scheme 1.Catalytic Synthesis of Glycosyl Chloride. Inset- Catalytic Appel Cycle

C.W. Chang, S.S. Chang, C.S. Chao, K.K.T. Mong, Tetrahedron Lett. 2009, 50, 4536.

S. Traboni, F. Liccardo, E. Bendini, M. Giordano, A. Iadonisi, Tetrahedron Lett. 2017, 58, 1762.

R.M. Denton, J. An, B. Adeniran, A.J. Blake, W. Lewis, A.M. Poulton, J. Org. Chem. 2011, 76, 6749.

I. Pongener, K.Nikitin, E.M. McGarrigle, submitted for publication.

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