Anomeric hydrogen, chemical reactivity

The major difference between C- and O-glycosides is found within chemical reactivities. Not only are C-glycosides absent of anomeric effects, they are also stable to acid hydrolysis and are incapable of forming hydrogen bonds. 

COf shows the expected selectivity for the anomeric hydrogens of methyl p-D-glucoside and cellobioside, reacting with the latter at a rate of 7 X 10 M s at 20 °C i.e. about five orders of magnitude slower than OH). However, when cellulose (as cotton linters ) was used as a substrate, hydrogen abstraction was indiscriminate, possibly because intrinsic chemical reactivities were counterbalanced by relative accessibility. ... 

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