Pyridine → HCID 57684693, compound

Participants

Reaction Steps

To a solution of Ph3PMeI (378 mg, 0.935 mmol) in toluene (3 mL) was added KN(TMS)2 (0.5 M, 1.8 mL) dropwise. After stirring for 40 min, (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (intermediate AY) (360 mg, 0.626 mmol) in toluene (5 mL) was added. After stirring overnight, the reaction was quenched with a saturated solution of NaHCO3. The mixture was extracted 3× with AcOEt. The combined organic extracts were washed 1× with brine prior to drying over Na2SO4. Concentration of the solution gave an oily residue, which was redissolved in 3 mL of CH2Cl2, and then 0.2 mL of pyridine (2.47 mmol), 0.23 mL of Ac2O (2.44 mmol) and DMAP (catalytic quantity) were added. The mixture was stirred for 2 h at room temperature. Additional CH2Cl2 (20 mL) was added, the mixture was washed 2× with 1N HCl and 1× with brine prior to drying over Na2SO4. Concentration of the solution and purification of the crude product by silical gel column gave intermediate AZ (286 mg).

Provenance & Evidence