Benzyl Bromide → HCID 15115713, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9.0 g. (0.034 mole) of methyl 5-O-(t-butyldimethylsilyl)-2-deoxyribofuranoside, 15 g (0.19 mole) of benzyl bromide, and 21 g (0.076 mole) silver carbonate in 50 ml dry dimethylformamide or other aprotic solvent is heated at 60° C. under a dry nitrogen atmosphere for five days. The mixture is cooled and the solids filtered. The filtrate is then concentrated at reduced pressure to 30 ml volume. To this are added 20 ml pyridine and the mixture heated at 65° C. for three hours. The solvents are again removed under reduced pressure affording a dark gummy residue which is taken up in a mixture of 150 ml toluene and 100 ml DI water. The organic phase is separated, washed with water (2×100 ml), dried (Na2SO4) and filtered. The solvent is removed at reduced pressure affording the methyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxyribofuranoside compound as a red oil.

Provenance & Evidence