August 05, 2021, 04:27:53 AM
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Topic: hydrolysis of isopropenyl αlpha-D-glucopyranoside  (Read 330 times)

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Offline myii

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hydrolysis of isopropenyl αlpha-D-glucopyranoside
« on: May 20, 2021, 07:20:53 AM »
Hi

Does anyone know where I can find the hydrolysis of isopropenyl αlpha-D- glucopyranosides?

Really struggling to find the mechanism for it :(

Thanks :)

Offline Babcock_Hall

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Re: hydrolysis of isopropenyl αlpha-D-glucopyranoside
« Reply #1 on: May 20, 2021, 10:34:19 AM »
Have you tried SciFinder?  Another way to approach this question is to think about the synthesis and apply the concept of microscopic reversibility.

Online rolnor

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Re: hydrolysis of isopropenyl αlpha-D-glucopyranoside
« Reply #2 on: May 20, 2021, 01:18:30 PM »
I am not sure about this structure, where is the isoprenyl attached?

Offline myii

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Re: hydrolysis of isopropenyl αlpha-D-glucopyranoside
« Reply #3 on: May 20, 2021, 02:06:51 PM »
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?

Offline Babcock_Hall

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Re: hydrolysis of isopropenyl αlpha-D-glucopyranoside
« Reply #4 on: May 20, 2021, 02:38:31 PM »
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.

Offline OrganicH2O

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Re: hydrolysis of isopropenyl αlpha-D-glucopyranoside
« Reply #5 on: May 20, 2021, 04:20:05 PM »
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.
I have a Master's in organic chemistry and I am exposed to a LOT of different introductory organic chem classes in the course of my work, ranging from very basic to Harvard. I am here to refine my knowledge and consult with other organic chemistry nerds.

Offline Babcock_Hall

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Re: hydrolysis of isopropenyl αlpha-D-glucopyranoside
« Reply #6 on: May 22, 2021, 11:19:11 AM »
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?

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