I have a steroid-like molecule containing 2 vicinal OH-groups (both in beta-configuration) in its A-ring, at the 2,3-position. I'd like to remove these two groups. So far I have already tried tosylation, but with no result at all. The molecule also contains two other OH-groups on another part of the molecule, but they are tertiary OH-groups, which didn't undergo any reaction of the same kind. In the reactions I used methylene-chloride as solvent, 2,2 eqv. (or 4,5 eqv.) of TsCl and 2,5 eqv. of pyridine. I started the reaction at 0°C and let it warm up to room temperature. No matter how long the reaction was going on, no change in the starting material has been observed. Now I tried the same with toluene as solvent at 80°C, but no results either.
Could it be a result of sterical hindrance? Should I try mesylation instead or some other method to remove these OH-groups?
Thank you very much for your answers!