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Deprotection of acetal
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Topic: Deprotection of acetal (Read 1022 times)
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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.
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rolnor
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Re: Deprotection of acetal
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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.
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wildfyr
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Re: Deprotection of acetal
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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.
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Babcock_Hall
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Re: Deprotection of acetal
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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.
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rolnor
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Re: Deprotection of acetal
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Reply #4 on:
March 03, 2022, 06:03:49 PM »
Its impossible to avoid mixture its bad PG-strategy
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Deprotection of acetal