An efficient approach to the synthesis of thymidine derivatives containing phosphate-isosteric methylene acetal linkages

Article abstract of DOI:10.1016/S0040-4020(01)86429-2

Iodonium ion promoted condensation of properly protected 3′-O-methylthiomethyl or 3′-O-(4-penten-1-oxymethyl)-thymidine with 3′-O-methoxyacetyl-thymidine, was explored. A judicious choice of the iodoinium source and protecting groups led to an efficient preparation of thymidine dimers having internucleosidic-3′5′)-methylene bonds. The latter procedure was utilized towards the synthesis, in solution and on a solid support, of DNA-fragments containing one or more T-_CII2-T dimers. Further, 5′-O-methylthiomethyl-3′-O-methoxyacetyl-N ³-benzoyl-thymidine proved to be a suitable donor for the introduction of 5′-O-methylene acetal-linkage s between 2,3,4,6-tetra-Obenzyl-D-glucose, benzyl N-benzyloxycarbonyl-L-serine and dibenzyl phosphate.