| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1388805 | Carbohydrate Research | 2013 | 8 Pages |
A new type of rearrangement is described for 3-C-branched chain aldoses. The studied transformation is based on the Mo(VI)-catalyzed isomerization of carbohydrate carbon skeleton and allows preparation of C-3 isomers of 3-C-branched aldoses in a simple way without formation of side products. This rearrangement at C-3 carbon differs from the previously described epimerization at C-2 of aldoses catalyzed by Mo(VI) ions, known as Bílik reaction. The potential of this new transformation is illustrated on the preparation of new, 3-C-methyl-d-glucose and 3-C-vinyl-d-glucose from 3-C-methyl-d-allose and 3-C-vinyl-d-allose, respectively.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A new type of rearrangement is described for 3-C-branched chain aldoses. ► The reaction is based on the Mo(VI)-catalyzed isomerization of carbon skeleton. ► Allows preparation of C-3 isomers of 3-C-branched aldoses in a simple way. ► The method leads to preparation of rare saccharides in a single step.
