Re: purifying phosphates on sugars

I do not know how relevant this is:

Long time ago I did derivatisation of natural phospholipis (for
analysis) and I needed to isolate a miligram quantity od
perfluorobutyrate-acylated glycerol mixed fatty ester-ethers.
Perfluorobutyrate being hydrolyticaly sensitive, I was only able to
observe these compounds on TLC but any attempt of isolation provided
mostly the hydrolyzed products - even with prep. TLC or very fast run
on a micro-column.

Diphenylphosphate on glycosidic O will be very unstable. Try to look up
Scifinder and Crossfire/Beilstein if anybody made this kind of compound
before. You may also try a prep chromatography on (boil-degassed)
charcoal, diphenyl phosphate being greasy could be retained more than
non-aromatic stuff. I would start in methanol and elute first with
gradient of ethyl acetate in MeOH and if the compounds does not come
off, then do toluene or benzene gradient.

The problem is that your compound will fall apart in protic media both
under acidic and basic conditions. Do you realy need to isolate it?

.