J. Mann et al., 2 SYNTHETIC ROUTES TO 3'-DIDEOXY-3'-C-(HYDROXYMETHYL)-4'-THIONUCLEOSIDES, Journal of the Chemical Society. Perkin transactions. I, (6), 1995, pp. 677-681
A number of 3'-dideoxy-3'-C-(hydroxymethyl)-4'-thionucleosides have be
en prepared from either rt-butyldimethylsiloxymethyl)tetrahydrofuran-2
-one or from R,3R)-1-benzyloxy-3(benzyloxymethyl)hex-5-en-2-ol. The fo
rmer was converted into methyl dimethylsiloxy)-3-(tert-butyldimethylsi
loxymethyl) and then into 1-0-acetyl-2,3-dideoxy-3-C- butyldimethylsil
yl)-4-thio-D-evythro-pentofuranose prior to coupling with silylated py
rimidines. The second key intermediate was converted into benzyloxymet
hyl-5,5-bis(benzylsulfanyl)pentan-2-ol and thence via the mesyl ester
into yl)-2,3-dideoxy-1,4-dithio-D-erythro-pentofuranose prior to coupl
ing with silylated pyrimidines.