The synthesis of oligoribonucleotides. II. The use of silyl protecting groups in nucleoside and nucleotide chemistry. VII

Abstract

The synthesis of oligonucleotides derived from uridine and adenosine using the tert-butyldimethylsilyl protecting group and the trichloroethylphosphorodichloridite condensation procedure is described. These procedures involve rapid preparation of protected starting materials and equally rapid condensation of units to form nucleotides. Optimum yields using collidine as base in tetrahydrofuran as solvent are between 65 and 80%. The utility of the procedure is rendered complete by the capability to remove both the phosphate protecting groups and the alkylsilyl groups in a single 30 min step using tetrabutylammonium fluoride in tetrahydrofuran.