Synthesis of 1,4-anhydro-2-deoxy-D-ribitol derivatives from thymidine.
1,2-Dideoxyribose 5-O-succinate, a component of solid support employed in the synthesis of ribozymes, was synthesized from thymidine. The key step was elimination of nucleobase from 2 to afford glycal 3. A number of catalysts for this reaction were tested, resulting in improved and scaleable synthesis. Hydrogenation of the resulting glycal afforded 1,2-dideoxyribose derivative 4 in a high yield.
Serebryany
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Ribozyme Pharmaceuticals Inc., Boulder, Colorado 80301, USA. serebru@rpi.com
Beigelman
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D003855:Deoxyribose / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D003855:Deoxyribose; C043138:1,2-dideoxyribofuranose; D013936:Thymidine