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I recently read a fact about glycosides:

Strong reagents like $\ce{C6H5NHNH2}$ or $\ce{NH2OH}$ are required to decompose it and acidic hydrolysis fails to do so.

Why is it so? What makes it different from other hemiacetals which can be decomposed by both acidic and alkaline hydrolysis?

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    $\begingroup$ You are missing the context there... $\endgroup$ – Mithoron Jun 15 '20 at 17:45
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This information is wrong. Glycosides do undergo acidic hydrolysis. The accepted mechanism of this hydrolysis is as follows1:

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References:

  1. Vernon, C. A. “The Mechanisms of Hydrolysis of Glycosides and Their Revelance to Enzyme-Catalysed Reactions.” Proceedings of the Royal Society of London. Series B, Biological Sciences, vol. 167, no. 1009, 1967, pp. 389–401. JSTOR.
  2. Timell, T. E. “The Acid Hydrolysis of Glycosides: I. General conditions and the effect of the nature of the aglycone.” Canadian Journal of Chemistry, vol. 42, no. 6, 1964, pp. 1456–72. doi:10.1139/v64-221.
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