Boron trifluoride etherate → HCID 86600676, compound

Participants

Reaction Steps

A solution of 0.48 g (approx. 88% pure) 1-(2,3,4,6-tetra-O-benzyl-1-hydroxy-D-glucopyranosyl)-3-[4-(tert-butyl-dimethyl-silyloxy)-benzyl]-4-methyl-benzene in 3.5 mL dry acetonitrile is cooled to −40° C. under argon. 0.13 mL triisopropylsilane and 0.08 mL boron trifluoride etherate are added dropwise. The solution is stirred for 3 h at −35° C., before another 0.02 mL of triisopropylsilane and 0.01 mL of boron trifluoride etherate are added. After a further 2 h at −40° C. aqueous potassium carbonate solution is added, and the resulting mixture is stirred for 1 h at ambient temperature. Then water is added and the mixture is extracted four times with ethyl acetate. The organic phase is dried over sodium sulfate, concentrated and chromatographed on silica gel (cyclohexane/ethyl acetate 10:1->4:1).

Provenance & Evidence