Ammonia → HCID 131719636, compound

1.09 g (1.41 mmol) of 1,6-anhydro-4-O-benzyl-2-deoxy-2-[1D-(1N,2,4/3)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 3) was dissolved in THF (20 ml) and liquid ammonia (~100 ml) was added at ~78° C. Sodium (0.42 g) was added and the reaction mixture was stirred for 30 minutes at this temperature. NH4 Cl(2 g) was then added and ammonia and THF were evaporated at room temperature. The residue was acetylated in pyridine (5 ml) and acetic anhydride (5 ml). Excess of acetic anhydride was quenched by the addition of methanol. The reaction mixture was evaporated and dissolved in dichloromethane (100 ml) and washed sequentially with 5% HCl solution (2×100 ml), saturated NaHCO3 solution (2×100 ml) and water (2×100 ml) before evaporation to a syrup. The syrup was purified by chromatography on silica gel using toluene:ethylacetate (3:1) as eluent to provide 1,6-anhydro-3-4-di-O-acetyl-2-deoxy-2-[1D-(1N,2,4/3)-(2,3,4-tri-O-acetyl-5-C-acetoxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 4) (613 mg, 75.8%).

1. customammonia and THF were evaporated at room temperature
2. customExcess of acetic anhydride was quenched by the addition of methanol
3. customThe reaction mixture was evaporated
4. dissolutiondissolved in dichloromethane (100 ml)
5. washwashed sequentially with 5% HCl solution (2×100 ml), saturated NaHCO3 solution (2×100 ml) and water (2×100 ml) before evaporation to a syrup
6. customThe syrup was purified by chromatography on silica gel

ORD record

ord-87e6e284e650473d89c0da2e228c43f7

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05814616