Sodium Azide → 3,4,6-Tri-O-Acetyl-2-Azido-2-Deoxy-alpha-D-Glucopyranosyl Bromide

Temperature

-30 °C

A 1 L flask containing 400 mL of acetonitrile was charged with sodium azide (7.75 g, 119.2 mmol) and ceric ammonium nitrate (120.7 g, 219.4 mmol). The resulting suspension was cooled to −30° C. and a solution of tri-O-acetyl-D-glucal (20.75 g, 76.22 mmol) in 100 mL acetonitrile was added to it dropwise. The reaction mixture was stirred at −30° C. for 20 hours and then warmed to room temperature, taken up in 800 mL of diethyl ether and washed with water (3×250 mL). The organics were dried over magnesium sulfate, filtered, and the solvent removed in vacuo to yield an oil. This oil was placed in a 1 L flask containing 400 mL of acetonitrile and lithium bromide (33.53 g, 386.1 mmol) and stirred at room temperature for at least 4 hours. The solvent was removed in vacuo and the resulting residue was taken up in 400 mL of dichloromethane. The organic layer was washed with water (2×250 mL), dried over magnesium sulfate and filtered. The solvent was removed in vacuo to yield the title compound as a gold oil which was used directly as in Example 1.

1. temperaturewarmed to room temperature
2. washwashed with water (3×250 mL)
3. dry with materialThe organics were dried over magnesium sulfate
4. filtrationfiltered
5. customthe solvent removed in vacuo
6. customto yield an oil
7. customThis oil was placed in a 1 L flask
8. stirringstirred at room temperature for at least 4 hours
9. customThe solvent was removed in vacuo
10. washThe organic layer was washed with water (2×250 mL)
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. customThe solvent was removed in vacuo

ORD record

ord-def47593b63f498ca072d2820590d911

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06670324B2