Re: ORGLIST:vinyl sulfone/acetate ester deprotection problem

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From: S.BARTOLI$##$soton.ac.uk
Date: Tue Jul 20 2004 - 07:28:33 EDT


Hi.
I do not know if it can be useful but I remember that some time ago I used DBU
(toluene, 60 C) to cleave an acetyl group.

Good Luck,

Sandra

Scrive "Henry, Lee" <henryg$##$cshl.edu>:

> Hi.
>
> I am wondering if anyone can provide advice on a deprotection problem
> that I
> have encountered. I have a molecule that possesses a diol protected by
> two
> acetyl esters and a vinyl sulfone. Attempts to remove the acetyl ester
> via
> the traditional K2CO3 in H2O/MeOH solvent destroy the vinyl sulfone as
> determined by its inability in another assay to participate in a
> simple
> michael addition. The molecule of interest was synthesized using
> acetyl
> ester protected alcohols because of commercial avialability from Sigma
> of a
> tartaric acid anhydride protected in this manner. The other option
> would be
> to use an ether protected precursor but in that case I was certain I
> could
> not deprotect the alcohol without effecting the vinyl sulfone.
>
> Does anyone know of a way to remove/deprotect the acetyl ester without
> effecting the vinyl sulfone. Might not be possible, but if it is can
> anyone
> advise me of how to proceed.
>
> Thanks
> Lee
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