Ammonia → HCID 53699921, compound

Participants

Reaction Steps

Methyl 3,5,6-tri-O-benzyl-2-O-heptyl-D-glucofuranoside (10.5 g, 0.019 mol) was dissolved in 25 ml of anhydrous ether and placed in a flask maintained at -40 to -50 C. in an acetone-dry ice bath. Ammonia (100 ml) was condensed into the flask, and 2.05 g (1.6 eq.) of sodium metal was added in small portions, until a deep blue color persisted. The excess sodium metal was quenched by the careful addition of solid ammonium chloride, and the mixture was allowed to warm up to room temperature with nitrogen sparging. The mixture was filtered, the residue was washed with acetone, and the combined filtrate and washings were evaporated to give a syrup which was purified by flash chromatography (70:30 ethyl acetate in hexane, then neat ethyl acetate) to afford 4.96 g (91.3%) of the title compound methyl-2-O-heptyl-D-glucofuranoside, roughly 4:5 as a mixture of alpha and beta anomers. NMR: 4.94 (d, H-1, alpha); 4.88 (s, H-1, beta); 3.41 (S, ome); 3.38 (s, ome) 1.28 (m, 8H, 4 CH2); 0.89 (t, 3H, CH3)

Provenance & Evidence