Stereospecific Synthesis of the α- and β-d-Glucopyranosyl Ureas
- 16 May 2001
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (12) , 4200-4205
- https://doi.org/10.1021/jo0100751
Abstract
A new, one-pot, two-stage procedure for the preparation of the α- and β-d-glucopyranosyl ureas has been developed. Oxidation of glucopyranosyl isocyanides provides glucopyranosyl isocyanates, which can be trapped in situ with amines to afford good yields of glucopyranosyl ureas. Application of this method establishes the successful synthesis of the hitherto unknown N,N‘-di-α,α- and α,β-d-glucopyranosyl ureas.Keywords
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