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Issue 32, 2019
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Synthesis of glycosyl chlorides using catalytic Appel conditions

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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.

Graphical abstract: Synthesis of glycosyl chlorides using catalytic Appel conditions

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Supplementary files

Article information


Submitted
11 Jul 2019
Accepted
26 Jul 2019
First published
01 Aug 2019

Org. Biomol. Chem., 2019,17, 7531-7535
Article type
Paper

Synthesis of glycosyl chlorides using catalytic Appel conditions

I. Pongener, K. Nikitin and E. M. McGarrigle, Org. Biomol. Chem., 2019, 17, 7531
DOI: 10.1039/C9OB01544B

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