| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1390992 | Carbohydrate Research | 2006 | 7 Pages |
Abstract
γ-Sugar-amino acid analogues in the form of C-ketosides can be prepared in 5–6 steps starting from d-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting β-cyano esters provides C-ketoside-based γ-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Frank Schweizer, Ole Hindsgaul,