Trifluoroacetic acid → HCID 59013481, compound

Participants

Reaction Steps

To (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-5-(4-ethylbenzyl)-2-vinylphenyl)tetrahydro-2H-pyran-2-ol (120 mg, 0.15 mmol) was added TFA (1.5 mL) at −10° C. After the reaction mixture was stirred for 6 h, the solvent was removed under vacuum and aqueous saturated NaHCO3 (10 mL) was added to the residue. The aqueous layer was extracted with EtOAc (10 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. Removal of the solvent afforded the crude product, which was dissolved in 1.9 mL of a mixture of THF:CH3OH:H2O (2:3:1) followed by addition of 6 mg of LiOH.H2O at room temperature. After stirring for 2 h, the volatiles were removed using a rotary evaporator. The residue, after being dissolved in ethyl acetate, was washed with brine (10 mL×2), 5% aqueous KHSO4 (10 mL) and finally with brine (10 mL) prior to drying over Na2SO4. The volatiles were removed and the resulting oil was purified by preparative TLC to obtain 44 mg of the title product.

Provenance & Evidence