An Efficient Synthesis of N-Allylglycosylamides from Unprotected Carbohydrates

Synthetic, multivalent, carbohydrate assemblies are important tools in studying the avidity of many naturally occuring lectins for their ligands. This report details a simple, high-yielding three-step procedure to convert unprotected carbohydrates into N -allylglycosides. This method compliments the reductive amination procedure but allows the reducing-end pyranose ring to remain intact. No carbohydrate protecting groups are needed, and the resulting N -allylglycosylamide can be easily linked to other molecules. Two examples of analogs of silyl Lewis x and sulfo Lewis x have been derivatized by this process.