Synthesis of glycosyl chlorides using catalytic Appel conditions
Imlirenla Pongener1, Kirill Nikitin1, Eoghan M McGarrigle1
1Centre for Synthesis and Chemical Biology, UCD School of Chemistry, University College Dublin, Belfield, Dublin 4, Ireland. eoghan.mcgarrigle@ucd.ie.
Abstract:
The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.
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