HCID 15546043, compound → HCID 57227701, compound

Participants

Reaction Steps

Referring to FIG. 9, 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyrimidine-4-one (3) was synthesized in accordance with Niedballa et al., J. Org. Chem 1974, 39, 3668-3671. 1-(β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one (5) was prepared by standard NaOMe/MeOH deprotection of derivative 3 with nearly quantitative yield. 1-(5-O-Dimethoxytrityl-β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one (6) was prepared by standard dimethoxytritylation of 5 in pyridine (rt., overnight) resulting in a yield of 83%. 1-(5-O-Dimethoxytrityl-2-O-tert-butyldimethylsilyl-β-D-Ribofuranosyl)-1,4-dihydropyrimidine-4-one was prepared using standard silylation procedure (Hakimelahi et al., Can. J. Chem. 1982, 60, 1106-1113). 1-[5-O-Dimethoxytrityl-2-O-tert-butyidimethylsilyl-3-O-2cyanoethyl-N,N-diisopropylaminophosphoramidite-β-D-Ribofuranosyl]-1,4-dihydro-pyrimidine-4-one (7) was prepared by phosphitylation using standard phosphitylation procedure (Tuschl et al., Biochemistry 1993, 32, 11658-11668).

Provenance & Evidence