Phase Transfer Catalysis as a General and Stereoselective Entry into Glycosyl Azides from Glycosyl Halides
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (07) , 618-620
- https://doi.org/10.1055/s-1992-26175
Abstract
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.Keywords
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