2,6-Lutidine → HCID 130761496, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-dideoxy-3-C-methyl-D-erythro-pentono-1,4-lactone (490 mg, 3.76 mmol) in methylene chloride (10 mL) cooled in an ice-bath were added 2,6-lutidine (501 mL, 4.30 mmol) and trifluoromethanesulfonic anhydride (682 mL, 4.05 mmol). The reaction mixture was stirred at 0° C. for 30 minutes, diluted with methylene chloride, washed with water, 2N hydrochloric acid, saturated sodium hydrogencarbonate solution, saturated brine solution, dried (Na2SO4), and evaporated. The crude product was taken up in DMF (6 mL) and treated with sodium azide (856 mg, 13.2 mmol) at room temperature for 30 minutes. The mixture was diluted with ethyl acetate, washed with water, dried (Na2SO4), and evaporated. The pure title compound was obtained after flash silica gel chromatography eluting with 25% ethyl acetate in hexane; yield 358 mg (61%); 1H NMR (400 MHz, CDCl3): δ1.15 (d, 3H), 2.21 (dd, 1H), 2.42 (m, 1H), 2.74 (dd, 1H), 3.44 (dd, 1H), 3.60 (dd, 1H), 4.15 (m, 1H); mass spectrum: 128 (M+1-N2).

Provenance & Evidence