Short synthesis of allyl 2-acetamido-2-deoxy-3,6-di-O-(α-L-fucopyranosyl)-β-D-glucopyranoside

Article abstract of DOI:10.1016/0008-6215(93)84047-A

As insect cells are being used for the production of recombinant proteins and glycoproteins, it has become important to investigate whether part structures, which are typically generated by these cells, could lead to adverse reactions upon administration of recombinant glycoproteins into vertebrate organisms. We have therefore set out to synthesize part structures of glycoprotein N-glycans bearing fucosyl residues in alternative linkages, in a form which provides access to haptens and immunogens for testing their immunogenic and antigenic potential. Best results were obtained using iodonium ion-assisted glycosylation with iodonium di-sym-collidinium perchlorate in dichloromethane-diethyl ether under inverse conditions.