Potassium Phosphate, Tribasic → (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate (56) (200 mg, 0.320 mmole) in toluene/water (4 mL/2 mL) were added trimethylboroxine (134 μL, 0.960 mmole), Pd(OAc)2 (7.2 mg, 0.0320 mmole), tricylcohexylphosphine tetrafluoroborate (23.6 mg, 0.0640 mmole), and K3PO4 (272 mg, 1.28 mmole). The mixture was stirred at 100° C. overnight. The reaction mixture was filtered through celite bed and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound 57 (125 mg, 0.223 mmole, 70%) as a yellow solid. [M+Na]+ 583.

Provenance & Evidence