I am interested in Chemical Glycosylation, specifically the production of cellulose by synthetic means. However, it is difficult to ensure that the glycosidic bond is formed between the 1 and 4 carbons.

Are there any techniques that can select for this reaction?

I am looking for good references on this subject.


You have to protect the OH groups you don't want to react with protecting groups.

In this case you could install a benzylidene acetale between the 4 and 6 OH, then protect all the other OH and then do selective reductive opening of the benzylidene so your benzyl group will be on position 6 and you got a free OH. That said: it's quite expensive, labor intensive and has very bad atom economy. And you might run into problems with deprotection once you got polymer structures, so that's not a feasible option for synthesis of cellulose.

I don't think it's possible to optimize a synthesis without protecting groups, so the best way would be doing it enzymatically, which could be very expensive too.


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