ORGLIST:vinyl sulfone/acetate ester deprotection problem

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From: Henry, Lee (henryg$##$
Date: Mon Jul 19 2004 - 14:00:45 EDT


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.

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