Synthetic methodology study reveals practical synthesis of 4′-thioribonucleosides from L-arabinose via ring contraction, indicating a streamlined route for therapeutic nucleoside analogues.
The detailed practical synthesis of 4'-thionucleosides starting from L-arabinose is described here. 1,4-Anhydro-2,3-O-isopropylidene-4-thioribitol, which is the key intermediate for the synthesis of 4'-thionucleosides, is obtained from L-arabinose in several steps, including a novel reductive ring-contraction reaction. After oxidation of the key intermediate, the sulfoxide is subjected to Pummerer-type thioglycosylation in the presence of persilylated nucleobases to obtain the 4'-thioribonucleosides in good yield and β-selectively.
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Wakamatsu et al. (2017) studied this question.
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