452310-83-7Relevant academic research and scientific papers
Reactions of 3′-C-halomethyl and 3′-C-sulfonylmethyl uridines with phosphinic acid derivatives - Synthesis of building blocks for oligonucleotides containing 3′-C-methylenephosphonate linkages
Winqvist, Anna,Stroemberg, Roger
, p. 1509 - 1515 (2007/10/03)
An efficient method for the synthesis of nucleoside 3′-C-methylenephosphinates, building blocks for oligo(ribo-nucleoside methylenephosphonate)s, has been developed. Treatment of bis(trimethylsilyl)hypophosphite (BTSP) with a 3′-deoxy-3-C-(iodomethyl)uridine resulted both in substitution to give the corresponding 3′-C-methylenephosphinate and in reduction of the iodomethyl group to afford the uridine 3′-deoxy-3′-C-methyl derivative. Optimisation of solvent and temperature gave a substitution/reduction ratio of 5:4 at best. Through the use of a trifluoromethanesulfonyl leaving group and further optimisation of reaction conditions, however, the triethylammonium 2′-O-(tert-butyldimethylsilyl)-3′-deoxy- 5′-O-(4-methoxytriphenylmethyl)uridine-3′-C-methylene-phosphinate was obtained in 93% isolated yield. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
