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- W1489543735 abstract "Abstract Ribonucleosides are converted into 2′‐deoxyribonucleosides in good yields by a four‐step procedure. Selective protection of the 3′‐ and 5′‐hydroxyl groups with 1,3‐dichloro‐1,1,3,3‐tetraisopropyl‐1,3‐disiloxane is followed by functionalization of the 2′‐hydroxyl group with phenoxythiocarbonyl chloride. Free radical–mediated reductive C2′–O2′ bond cleavage of these 3′,5′‐ O ‐TPDS‐2′‐ O ‐PTC‐nucleoside derivatives with tributyltin hydride, followed by removal of the silyl protecting group with tetrabutylammonium fluoride, provides the 2′‐deoxyribonucleosides. Adenosine, cytidine, guanosine, and uridine are converted into dA, dC, dG, and dU in overall yields of 60% to 80%. Use of tributyltin deuteride in the reductive cleavage step gives 2′‐deuterio‐2′‐deoxyadenosine in 81% yield from adenosine with >85% retention of configuration at C2′. Application of this four‐step protocol with nucleoside analogs is straightforward." @default.
- W1489543735 created "2016-06-24" @default.
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- W1489543735 date "2005-06-01" @default.
- W1489543735 modified "2023-09-24" @default.
- W1489543735 title "Reduction of Ribonucleosides to 2′‐Deoxyribonucleosides" @default.
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- W1489543735 doi "https://doi.org/10.1002/0471142700.nc0111s21" @default.
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