Org. Lett., 9 (12), 2285 -2288, 2007. 10.1021/ol0705503 S1523-7060(07)00550-0
Web Release Date: May 10, 2007

Copyright © 2007 American Chemical Society

Oligosaccharide Synthesis in Microreactors

Frédéric R. Carrel, Karolin Geyer, Jeroen D. C. Codée, and Peter H. Seeberger*

Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland

seeberger@org.chem.ethz.ch

Received March 5, 2007

Abstract:

Described is the combination of microreactors and fluorous phase chemistry to assemble oligosaccharides. The synthesis of a -(16) linked D-glucopyranoside homotetramer serves to illustrate this approach. Glycosylations employing a Fmoc-protected glucosyl phosphate building block were performed in a silicon-based micro-structured device to optimize reaction conditions and for reaction scale-up. A perfluorinated linker at the reducing end of the oligosaccharides allowed for purification by fluorous solid-phase extraction (FSPE) and further functionalization.

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