Methanol → HCID 54143581, compound

A solution of methyl 5-O-methyl-D-ribofuranoside (Dubois L. et al. Tetrahedron 1993, 49(4), 901-910, 2 g, 11.2 mmol) in dimethylformamide (10 mL) was added dropwise to a suspension of sodium hydride (60% in oil, 2.25 g, 563 mmol) in dimethylformamide (54 mL). After stirring at rt for 45 minutes, a solution of benzyl bromide (4 mL, 33.6 mmol) was added dropwise in dimethylformamide (4 mL). The reaction mixture was stirred at rt overnight, quenched with methanol and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium chloride. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica, hexanes/ethyl acetate 70/30 to 50/50) to provide the a anomer (2.86 g, 71%) and the β anomer (0.86 g, 21%); α anomer Rf=0.5, β anomer Rf=0.4 (silica, hexanes/ethyl acetate 50/50).

1. stirringThe reaction mixture was stirred at rt overnight
2. customquenched with methanol
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate
5. washwashed with saturated aqueous sodium chloride
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash chromatography (silica, hexanes/ethyl acetate 70/30 to 50/50)
9. customto provide the a anomer (2.86 g, 71%)

ORD record

ord-e2cf0e7884c0445da86552e060855542

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05763596