Organic Letters 2001-10-18

Commercially available 5'-DMT phosphoramidites as reagents for the synthesis of vinylphosphonate-linked oligonucleic acids.

S Abbas, R D Bertram, C J Hayes

Index: Org. Lett. 3(21) , 3365-7, (2001)

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Abstract

[reaction: see text]. Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of each of these with the thymidine-derived vinylbromide 2 afforded the corresponding vinylphosphonate-linked dimers TT, d(C)T, d(A)T, and d(G)T in modest to good yields. The TT dimer was further elaborated to give a 5'-DMT-TT-3'-CEP building block, and this was used in the automated synthesis of the TpTTpT tetramer.

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  • Vinylphosphonic ac...

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