Synthesis of the Sugar Building Block of Bicyclo-RNA

Haziri, Arben I.; Silhar, Peter; Renneberg, Dorte; Leumann, Christian J. (2010). Synthesis of the Sugar Building Block of Bicyclo-RNA. Synthesis - journal of synthetic organic chemistry, 2010(05), pp. 823-827. Stuttgart: Thieme 10.1055/s-0029-1218650

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We present the novel synthesis of two sugar units that are central intermediates for the formation of members of the bicyclo-DNA and -RNA family. The synthesis starts from commercially available 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose. The key step involves the elaboration of a carbocyclic ring in a furanoside by rhodium(I)-catalyzed hydroacylation. Via this pathway, one of the sugar units is available in 8 steps and in an overall yield of 27%, while its deoxy derivative is obtained in 11 steps, which is 5 steps fewer than in our previous synthesis of this compound.

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