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silylation and desilylation reviews or information

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Babcock_Hall: 1972 "Silylation of organic chemicals" by Charles Roth 2017

One of our synthetic targets this summer requires us to use silylation of a derivative of glucose, and we will initially use the tert-butyldimethylsilyl group, as per wildfyr's suggestion.  We will need to deprotect in the presence of a vinyl sulfone.   In the past I used to use cesium fluoride to deprotect a primary alcohol that was trimethylsilylated; in this case I was planning to use TBAF.  I have done a little bit of reading in Greene and Wuts's book on protecting groups, and that raised a few questions.  I have turned up one or two old papers, and one open access chapter, the second link above.  Perhaps some additional background reading would help us.  Would anyone care to recommend a good review article or book chapter?

If your compound is sensitive, you should be ware that the reaction mixture becomes very alkaline when you desilylate with the reagents you suggest, if you want to avoid this you can use pyridine-HF or similar acidic fluoride source.

That's a good point. When I worked with CsF, it was dissolved in methanol, and our product was a primary alcohol.  If methanol became deprotonated (presumably an equilibrium mixture of alcohols and alkoxide ions was present), it would produce a decent nucleophile.  That might cause problems.

I have not previously encountered pyridine•HF, but I just looked it up and saw it referred to as the Olah reagent.  I trust that there is not a problem with toxicity.

Its really bad to get on skin, painfull burns, pain can remain for long time. I think there is also triethylamine trihydrofluoride that can be used, this is probably less nasty I would guess.


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