Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1384635 | Carbohydrate Research | 2010 | 8 Pages |
Abstract
2-Acetamido-2-deoxy-d-galactose (d-GalNAc) is an important monosaccharide widely distributed in nature. However, unlike its 4-epimer, the 2-acetamido-2-deoxy-d-glucose (d-GlcNAc), d-GalNAc is very expensive to obtain from commercial sources. Herein we report an efficient transformation that allows for the conversion of d-GlcNAc to a d-GalNAc derivative 7 in three steps and in 58.4–75% overall yields. The process was carried out on a greater than 20-g scale without the need of chromatography. The versatility of compound 7 was demonstrated by the synthesis of several useful monosaccharides and thiodisaccharides containing a d-GalNAc residue.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jianhao Feng, Chang-Chun Ling,