Pivaloyl chloride → HCID 10941025, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of D-glucose 42 (500 mg, 2.77 mmol) in 25 mL of pyridine is added pivaloyl chloride (3.42 mL, 3.34 g, 27.75 mmol) followed by DMAP (34 mg, 0.27 mmol). The reaction mixture is heated at 100° C. for 12 h, cooled to room temperature and quenched with 2 mL methanol. The reaction mixture is concentrated and the resulting residue is taken up in 25 mL CH2Cl2, washed with 1N HCl (3×25 mL), saturated NaCl (25 mL), dried over Na2SO4, filtered, concentrated and purified by flash chromatography (10% EtOAc/hexane) to afford 1.49 g (90%) of 1,2,3,4,6-penta-O-pivaloyl-β-D-glucopyranose 43: Rf 0.18 (5% EtOAc/hexane); 1H NMR (CDCl3, 270 MHz) δ 5.69 (d, J=8.2 Hz, 1H, H-1), 5.37 (app t, J=9.2 Hz, 1H, H-3), 5.21 (app t, J=8.7 Hz, 1H, H-4), 5.16 (app t, J=9.5 Hz, 1H, H-2), 4.06-4.17 (m, 2H, H-6), 3.86 (ddd, J=9.8, 4.8, 2.3 Hz, 1H, H-5), 1.21 (s, 9H), 1.17 (s, 9H), 1.15 (s, 9H), 1.12 (s, 18H).

Provenance & Evidence