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3′-α-Carboxymethyl-2′-O-methyl ribonucleosides, which are important building blocks for the construction of high affinity amide modified antisense oligonucleotides, have been synthesized from the corresponding 2′-O-methyl ribonucleosides via catalytic hydrogenation of their 3′-deoxy 3′-methoxycarbonyl-methylidene derivatives. Reduction of the olefinic double bond proceeds in good to excellent yields...
6 -α-Methyl and 6 -α-hydroxymethyl carbocyclic thymidines 11 and 22 have been synthesized via bicyclic lactone 2 and amines 9 and 19, respectively, as key intermediates. Both nucleoside analogs were subsequently elaborated into 5 -O-DMTr protected 3 -phosphoramidites of 6 -α-methyl and 6 -α-hydroxymethyl carbocyclic thymidines as well as appropriately base protected 5-methyl 2 -deoxycytidines...
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