[Guitarmaniac86]

Hi,

I am at a loss here and am looking for advice. I want to add uracil to my ribose sugar using the mitsunobu protocol as I have been using it for adding purines on but I cannot really find any literature on it.

In the past I have used vorbruggen conditions whereby I silylated the uracil with N,O-BSA then in situ added the sugar and the lewis acid.

Can I silylate the nucleobase and use it in Mitsunobu conditions? It just seems simpler to go via this route instead of functionalising the anomeric OH for utility in the vorbruggen conditions.

Thanks

[TheUnassuming]

If you are already using the Misunobu for purines successfully, why not try it with uracil on small scale to see what happens?  I can't imagine it hasn't been tried already, but who knows.   

[Guitarmaniac86]

I tried this reaction and it didn't work so I am going back to the drawing board. I'm posting this as an update just in case anyone else in the future has the same question.