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.

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In a previous communication,2 we reported that 1,8-dilithionaphthalene reacts with elemental sulfur, selenium, and

A series of phosphorodichloridites bas been prepared incorporating the most commonly used phosphate protecting groups in oligonucleotide synthesis. The groups include trichloroethyl, tribromoethyl, cyanoethyl, benzyl, methyl, p-chlorophenyl, and nitrophenethyl. The trichloroethyl and the nitrophenethyl appear to be the most stable groups while the cyanoethyl and methyl offer specific advantages. The benzyl and p-chlorophenyl groups are subject to limitations on their utility. Condensations can be carried out in a range of solvents including THF, pyridine, and DMF and at temperatures from −78 °C to 20 °C with a slight drop in yield with increasing temperature, at least for dinucleotide condensations.

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