Phase Transfer Catalysis as a General and Stereoselective Entry into Glycosyl Azides from Glycosyl Halides

François D. Tropper; Fredrik O. Andersson; Stéphane Braun; René Roy

doi:10.1055/s-1992-26175

Synthesis 1992; 1992(7): 618-620
DOI: 10.1055/s-1992-26175

short paper

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Phase Transfer Catalysis as a General and Stereoselective Entry into Glycosyl Azides from Glycosyl Halides

François D. Tropper^* , Fredrik O. Andersson, Stéphane Braun, René Roy

^*Department of Chemistry, University of Ottawa, Ottawa, Ontario, K1N 6N5, Canada

Abstract

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Peracetylated glycosyl- and glycobiosyl bromides and chlorides 1-5 including acetochloroneuraminic acid 6 were converted to their corresponding glycosyl azides 7-12 in 93-98% yields under phase transfer catalyzed conditions. The stereoselective reactions occurred with complete inversion at the anomeric centers to provide a general, high-yielding entry into 1,2-trans-glycosyl azides together with α-sialic acid azide.

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