HCID 18650251, compound → HCID 21309194, compound

Participants

Reaction Conditions

Reaction Steps

3'-O-t-Butyldimethylsilyl thymidine 4'-aldehyde (5.0 g; azeotroped twice with toluene, 25 ml) was dissolved in dry THF (60 ml) and cooled to -78° C., followed by addition of 1.0M solution of vinylmagnesium bromide (2.5 eq.) in THF. The reaction mixture was stirred for 30 minutes and then quenched with saturated aqueous NH4Cl, diluted with ethyl acetate, washed with water (2×100 ml) and then with brine. Then the organic layer was dried. The title compound was purified by flash chromatography using 30% ethyl acetate/hexane, affording a 43% yield of the desired alcohol.

Provenance & Evidence