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Topic: Synthesis using protecting groups  (Read 6256 times)

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Offline Rutherford

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Re: Synthesis using protecting groups
« Reply #15 on: January 01, 2016, 10:22:40 AM »
TBS group for O1.

Not sure how to deprotect O5, leaving other groups intact.
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Offline Dan

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Re: Synthesis using protecting groups
« Reply #16 on: January 01, 2016, 05:43:39 PM »
Quote from: Rutherford on January 01, 2016, 10:22:40 AM
Not sure how to deprotect O5, leaving other groups intact.

Why do you need the other groups to stay intact?
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Offline Rutherford

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Re: Synthesis using protecting groups
« Reply #17 on: January 02, 2016, 06:37:21 AM »
On methylation they will also react.
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Offline Dan

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Re: Synthesis using protecting groups
« Reply #18 on: January 02, 2016, 07:39:40 AM »
You can demethylate the O5 acetal in the presence of a methyl ether at O4 (your numbering).

The most straightforward strategy I see is to protect O1-3 (O5 is already protected as an acetal), methylate O4, then remove all protecting groups.
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Offline Rutherford

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Re: Synthesis using protecting groups
« Reply #19 on: January 02, 2016, 08:32:15 AM »
Ah, okay, I understood now.
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