[polymerase]

if i have a molecule, lets say 2-hydroxypropanoic acid, if i added TMS (a protecting group for alcohols) will the TMS:

(1) only protect the -OH on the 2nd carbon and NOT the -OH on the carbonyl

OR

(2) with protect both the -OH on the 2nd carbon and carbonyl

Not really sure which it should be...

Thanks!

[nj_bartel]

1

[alphahydroxy]

Yeah, it will protect the hydroxyl group, as opposed to the hydroxyl part of the acid - the former is an alcohol, the latter is not...

[sjb]

Depending on how it protects, I'd suggest that in fact it does act on both alcohol and carboxylic acid hydroxyls, but the carboxylic acid may very well be then deprotected in situ, especially with things like TMS-Cl (byproduct HCl).

Thoughts?

[alphahydroxy]

Depending on how it protects, I'd suggest that in fact it does act on both alcohol and carboxylic acid hydroxyls, but the carboxylic acid may very well be then deprotected in situ, especially with things like TMS-Cl (byproduct HCl).

Thoughts?

I'm not sure... I guess it's possible, but I think the low nucleophilicity of the acid relative to the alcohol would probably prevent this... If it were the case, one might expect to come across silylated acids more often...