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Topic: Hydrolysis of C2deoxy-glycosides  (Read 3696 times)

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Osel

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Hydrolysis of C2deoxy-glycosides
« on: September 26, 2004, 02:55:02 PM »
If a sugar is deoxy at C2 and has a glycosidic bond at the anomeric oxygen, will the hydrolysis of the glycosidic bond be slower or faster compared to the same sugar which has the OH group at C2?  Our readings seem to say that deoxy sugars are easier to hydrolyze, but this doesn't make sense - because the hydrolysis goes through a carbocation intermediate, it seems that having a donating group at C2 would cause faster hydrolysis?  
« Last Edit: September 26, 2004, 03:01:51 PM by Osel »

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