Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1383867 | Carbohydrate Research | 2013 | 8 Pages |
Abstract
The anti-thromboembolic pentasaccharide Fondaparinux was synthesized in 36 steps for the longest linear route, with 0.017% overall yield from d-glucose. Only three kinds of protecting groups were used for hydroxyl protection, Bn, Ac, and Bz, to accomplish this complex synthesis without decreasing the synthetic efficiency. Three l-idopyranosyl donors were investigated. Thioethyl glycoside is an efficient donor for l-idopyranosyl glycosylation with full α-selectivity, while l-idopyranosyl trichloroacetimidate resulted in poor α/β selectivity. A practical synthesis of key intermediate 1,6-anhydro-l-idopyranose 17 by H+/β-CD catalyst was developed.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Feng Lin, Gaoyan Lian, Ying Zhou,