Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: myii on May 20, 2021, 07:20:53 AM
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Hi
Does anyone know where I can find the hydrolysis of isopropenyl αlpha-D- glucopyranosides?
Really struggling to find the mechanism for it :(
Thanks :)
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Have you tried SciFinder? Another way to approach this question is to think about the synthesis and apply the concept of microscopic reversibility.
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I am not sure about this structure, where is the isoprenyl attached?
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Have you tried SciFinder? Another way to approach this question is to think about the synthesis and apply the concept of microscopic reversibility.
How can I find the mechanism on scifinder?
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I am not sure about this structure, where is the isoprenyl attached?
The OR group is on carbon-1. In the Haworth representation of α-D-glucose and its glucosides, the OR group is on the opposite side of the ring, relative to the CH2OH group on carbon-5. In the β-diastereomer, they are on the same side of the ring. I think that it is the isopropenyl group, not the isoprenyl group, but Spell Checkers are like Forest Gump's box of chocolates; you never know what you are going to get.
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The mechanism is going to depend slightly on the conditions. Is it a simple acid catalyzed hydrolysis? If yes, first you need to identify the functional group being hydrolyzed. Then, google or look up in a textbook the mechanism for that type of hydrolysis. A scifinder search might be unnecessary, and it might be hard to find such a basic mechanism in the literature when it is freely available in hundreds of textbooks.
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Have you tried SciFinder? Another way to approach this question is to think about the synthesis and apply the concept of microscopic reversibility.
How can I find the mechanism on scifinder?
Rather than using SciFinder, it will be easier to look it up in your textbook. Glycosides are a subclass of what class of molecules. In other words what functional group is present at C-1?