Glycosylation in room temperature ionic liquid using unprotected and unactivated donors

CARB 78

Tae-Joon Park, parkt@rpi.edu1, Michel Weiwer, parkt@rpi.edu2, Xuejun Yuan, yuanx@rpi.edu2, and Robert J. Linhardt, linhar@rpi.edu3. (1) Departments of Chemical and Biological Engineering, Rensselaer Polytechnic Institute, Biotech Center 4005,110 8th Street, Troy, NY 12180, (2) Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12180, (3) Department of Chemistry, Chemical & Biological Engineering, Biology, Rensselaer Polytechnic Institute, Troy, NY
Glycosylation using unprotected and unactivated donors is often preferable as it can reduce the number of steps, enhance reactivity, allow for a different stereochemistry, and increase prospects for further process modifications. The chemical synthesis of unprotected carbohydrates affords a number of challenges, including their poor solubility in most conventional organic solvents. Therefore, it is important to investigate new solvent systems that dissolve carbohydrates, support glycosylation reactions of unprotected sugars, and facilitate product recovery. Room temperature ionic liquids (RTILs) are becoming increasingly used as solvents for a wide variety of chemical reactions. These ionic solvents have the potential of replacing conventional volatile organic solvents in carbohydrate chemistry. In this work, we report the glycosidation of various simple, unprotected monosaccharides in RTILs to give benzyl glycosides, disaccharides, and oligosaccharides. RTILs facilitate the use of unactivated and unprotected donors in these reactions, resulting in a simple synthetic strategy involving a single glycosylation step.
 

General Posters
6:00 PM-8:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Carbohydrate Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007