Phosphate → HCID 13361982, compound

Benzyloxyacetaldehyde (80 mg, 0.53 mmol) in ) in ) 0.5 mL of acetonitrile, was added to 9 mL of a solution of antibody 38C2 (35 mg, 0.23 mmol) in PBS (phosphate buffer saline, 100 mM), followed by the addition of of hydroxyacetone. (0.5 mL, 6.3 mmol). After 48 hr at room temperature the reaction reached 56% conversion and the mixture was freeze dried. The remaining residue was extracted with methylene chloride. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, ethyl acetate/hexane, 1/1) to give pure 2111α (39 mg, 0.17 mmol, 32%) in 97% ee. Benzyl ether 2111α (39 mg, 0.17 mmol) was dissolved in 1 mL of methanol and hydrogenated with a catalytic amount of palladium hydroxide on carbon. After two hr, the mixture was filtered through celite and the solvent was removed under reduced pressure to give pure 1-deoxy-L-xylulose 1111 (19 mg, 0.14 mmol, 81%).

1. customdried
2. extractionThe remaining residue was extracted with methylene chloride
3. customThe solvent was removed under reduced pressure
4. customthe crude product was purified by column chromatography (silica gel, ethyl acetate/hexane, 1/1)
5. customto give pure 2111α (39 mg, 0.17 mmol, 32%) in 97% ee
6. waitAfter two hr
7. filtrationthe mixture was filtered through celite
8. customthe solvent was removed under reduced pressure

ORD record

ord-4c81263837f242a5a8da99e13b8c053d

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06326176B1