8-Methoxypsoralen → 1-[5-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione

Participants

Reaction Steps

For example, the furan-side monoadduct between thymidine and 8-methoxypsoralen, prepared as described above, is reacted with 4,4'-dimethoxytrityl chloride at room temperature in an appropriate anhydrous solvent to give the 5'-dimethoxytrityl thymidine:8-methoxypsoralen monoadduct. Following purification by high pressure liquid chromatography this compound is reacted with chloro-N,N diisopropylamino methoxyphosphine at room temperature in an appropriate solvent to give the 5'-dimethoxytritylthymidine phosphoramidite: 8-methoxypsoralen monoadduct. This compound is then used as an activated protected nucleoside phosphoramidite in a typical phosphite triester polynucleotide synthesis. The stereochemistry of the 8-methoxypsoralen moiety is correct (i.e. cis-syn) for subsequent crosslink formation when hybridized to the complementary sequence.

Provenance & Evidence