The 1,2-dianisyl-2,2,2-trichloroethyl group as 2'-hydroxyl protection of ribonucleotides

Article abstract of DOI:10.1016/0040-4020(95)00981-7

The 1,1-dianisyl-2,2,2-trichloroethyl group (DATE, 1) was introduced as a new 2'-hydroxyl protecting group of ribonucleotides. The usefulness of DATE as a 2'-OH protection was demonstrated in the solid phase synthesis of a dinucleotide by the phosphoramidite method. Starting from 2'-O-DATE-uridine (5), a suitable protected building block 7 was thus prepared and condensed in a conventional DNA synthesizer with the unprotected 5'-hydroxyl group of thymidine bound to a support via the 3'-hydroxy group. The resulting chimeric dinucleotide was cleaved from the support and the protecting groups were removed to yield 8. Cleavage of DATE was performed by means of lithium cobalt(I)phthalocyanine smoothly and quantitatively without any by-product formation.