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Topic: Deprotection of acetal  (Read 1013 times)

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Offline Humr

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Deprotection of acetal
« on: March 03, 2022, 01:00:33 PM »
Hello. I would like to ask if someone has experience with deprotection of acetal in presence of esters. I  have molecule with 2 acetyls, one propargyl ester and galactose protected with acetons on it.

Offline rolnor

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Re: Deprotection of acetal
« Reply #1 on: March 03, 2022, 01:13:06 PM »
Its very hard to avoid hydrolysis of the esters, acetyls are so small. You will get mixture, I am convinced of that. Its bad PG-strategy you have.

Offline wildfyr

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Re: Deprotection of acetal
« Reply #2 on: March 03, 2022, 01:22:24 PM »
Acetals are probably less acid stable than ester groups, so you can try a weakly acidic solution for deprotection. Timing will matter.

Offline Babcock_Hall

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Re: Deprotection of acetal
« Reply #3 on: March 03, 2022, 03:57:57 PM »
For relatively simple acetals Dowex-50 (H+) is sometimes used, because it can be removed by filtration, which is quick and convenient.  However, I don't see how this would completely avoid the problems that wildfyr and rolnor have indicated.

Offline rolnor

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Re: Deprotection of acetal
« Reply #4 on: March 03, 2022, 06:03:49 PM »
Its impossible to avoid mixture its bad PG-strategy

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