Ammonia → HCID 53699921, compound

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)

1. customplaced in a flask
2. temperaturemaintained at -40 to -50 C
3. additionwas added in small portions, until a deep blue color
4. customThe excess sodium metal was quenched by the careful addition of solid ammonium chloride
5. filtrationThe mixture was filtered
6. washthe residue was washed with acetone
7. customthe combined filtrate and washings were evaporated
8. customto give a syrup which
9. customwas purified by flash chromatography (70:30 ethyl acetate in hexane

ORD record

ord-183adf9e848c4cf88f7fe8952b66a7b0

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05010058