Session:
PS2 Poster session 2 Even numbers
Code:
P182
Location (hall):
Foyer
Start/end time:
Tuesday, July 2, 2019 - 15:45 to 17:15
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
References:
- 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.
