Dess–Martin oxidation work up I'm doing an oxidation of an alcohol with Dess–Martin periodinane which works really well but having trouble with the work up. Doing this reaction with about 5 g of alcohol so the reaction ends up using about 17 g of DMP. As the reaction progresses the DMP byproduct crashes out. And working up turns it into a gun that is quite difficult to remove

Running reaction in DCM and work up with bicarb. Even after filtration DMP is still present. Separates fine on a column but with how much there is it seems to be trappings some of my product.  I've read that a thiosulphate wash is also used in these reactions, but I don't think this will be useful to get rid of the gum.

Any suggestions?
It looks like you are not the first to get gummed up by the mono-acetoxy iodinane byproduct of this reaction. A seemingly simple solution is given in this article about converting an alcohol to ketone via DMP:  


  The mono-acetoxy iodinane by-pdt can be converted to easier to remove by-pdts during workup by treatment with aq $\ce{NaOH}$ or $\ce{Na2S2O3}$.  


This is not a procedure I have experience with specifically, so I hope this a do-able solution for your problem as I understand it.  Good luck regardless.