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Full Paper
Fluorous-Assisted One-Pot Oligosaccharide Synthesis
Article first published online: 27 JAN 2010
DOI: 10.1002/ejoc.200901155
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Yang, B., Jing, Y. and Huang, X. (2010), Fluorous-Assisted One-Pot Oligosaccharide Synthesis. European Journal of Organic Chemistry, 2010: 1290–1298. doi: 10.1002/ejoc.200901155
Publication History
- Issue published online: 16 FEB 2010
- Article first published online: 27 JAN 2010
- Manuscript Received: 13 OCT 2009
Funded by
- National Institutes of Health. Grant Number: R01-GM-72667
- National Science Foundation. Grant Number: CHE0852308
Keywords:
- Carbohydrates;
- Fluorous separation;
- Hydrazones;
- Immobilization;
- One-pot synthesis
Graphical Abstract
A new “catch” and “release” method for oligosaccharide assembly that combines one-pot synthesis and fluorous solid-phase extraction was developed. A branched trisaccharide and a linear tetrasaccharide were synthesized rapidly in this fashion without the need for any silica gel chromatography.
Abstract
A new method for oligosaccharide assembly that combines the advantages of one-pot synthesis and fluorous separation is described. After one-pot glycosylations are completed, a fluorous tag is introduced into the reaction mixture to selectively “catch” the desired oligosaccharide, which is rapidly separated from non-fluorous impurities by fluorous solid-phase extraction (F-SPE). Subsequent “release” of the fluorous tag and F-SPE achieved the purification of the desired oligosaccharide without the use of time- and solvent-consuming silica gel chromatography. Linear and branched oligosaccharides have been synthesized with this approach in just a few hours (for the overall oligosaccharide assembly and purification process).