Synthesis of Ganglioside Mimics for Binding Studies with Myelin‐Associated Glycoprotein (MAG)*

* Dedicated to the memory of late Professor Jacques H. van Boom.

Abstract

Glycosylation of 3‐O‐unprotected 2‐azido‐2‐deoxy‐galactopyranoside (compound 5) with O‐(2,3‐di‐O‐acyl‐4,6‐O‐benzylidene‐D‐galactopyranosyl) trichloroacetimidates (compounds 4A, B) as glycosyl donors afforded β (1–3)‐linked disaccharides (9A, B) in high yield. Removal of the 2,3‐O‐acyl groups and selective 3‐O‐alkylation with α‐benzyloxycarbonyl‐alkyl triflates furnished the protected target molecules, which could be readily transformed into the desired ganglioside mimics.

* Dedicated to the memory of late Professor Jacques H. van Boom.

Keywords:

• Carbohydrate mimics
• Glycosidation
• O‐Alkylation
• Trifluoromethanesulfonates
• MAG
• Inhibition

Acknowledgments

This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

Notes

* Dedicated to the memory of late Professor Jacques H. van Boom.