Immobilized glycosyl acceptor

The first polymer-supported oligosaccharide synthesis by Schuerch s group employed the Koenigs-Knorr reaction and its variants, using an immobilized glycosyl acceptor on an organic solid polymer (Scheme 1) [14]. It was followed by inves-... 

Scheme 5.10 Application of NPGs in solid-phase synthesis (a) immobilization of the glycosyl donor (b) immobilization of the glycosyl acceptor.66...

Immobilized 38 also proved to be an appropriate glycosyl acceptor when coupled with a full benzylated trichloroacetimidate donor (Scheme 10.8). Thus, TMSOTf mediated coupling of 38 with an excess of 48 gave resin-bound 49, which was further coupled with acceptor 38 to give trisaccharide 60 (60% overall yield based loading of the resin). 

Boons and coworkers have used the polystyrylboronic acid as a temporary polymeric support for oligosaccharide synthesis (Scheme 16.3). Polystyrylboronic acid 5, easily prepared from the corresponding bromide by treatment with trimethyl borate and n-BuLi in high loading capacity, was introduced on the 4,6-0 positions of the acceptor 6 by heating in pyridine. The immobilized boronate acceptor 7 was glycosylated with thioglycoside donor... 

Nicolaou [47] has applied this methodology in synthetic studies towards the antibiotic everinomicin 13,384-1. Glycosylation of immobilized fluoride donors such as 258 (Scheme 65) with sugar acceptors allowed the synthesis of disaccharides such as 259, attached to solid support through a selenium fink-... 

Figure 3. Immobilized a 1-4 glucosyltransferase reaction with soluble polymeric acceptors followed by photochemical release of saccharides from the polymers. M indicates glycosyl residues added by transfer.

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