Dimethylformamide → HCID 14585268, compound

10.5 g of 1,6-anhydro-3,4-dideoxy-2-O-(p-toluene)sulfonyl-β-D-threo-hex-3-enopyranose obtained in the above reaction, was dissolved in 100 ml of dried dimethylformamide, and 6 g of sodium benzoate was added thereto. The mixture was refluxed under heating for 30 minutes. The solvent was distilled off under reduced pressure, and 200 ml of water was added to the residue. The mixture was extracted with 300 ml of chloroform. The organic layer was washed once with 200 ml of a saturated sodium hydrogencarbonate aqueous solution and then washed twice with 200 ml of a saturated sodium chloride aqueous solution. Then, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the obtained syrup crude product was dissolved in 100 ml of dry methanol. Then, 2 ml of a methanol solution of sodium methoxide (28 wt %) was added thereto. The mixture was stirred for 25 minutes at room temperature. The reaction solution was neutralyzed with a 20% citric acid aqueous solution and then filtered through Celite® to remove the precipitate. The filtrate was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate: hexane=1:2) to obtain 1.1 g of the desired product (Compound No. 103). The NMR analytical data of this product are as follows.

1. temperatureThe mixture was refluxed
2. temperatureunder heating for 30 minutes
3. distillationThe solvent was distilled off under reduced pressure, and 200 ml of water
4. additionwas added to the residue
5. extractionThe mixture was extracted with 300 ml of chloroform
6. washThe organic layer was washed once with 200 ml of a saturated sodium hydrogencarbonate aqueous solution
7. washwashed twice with 200 ml of a saturated sodium chloride aqueous solution
8. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
9. distillationThe solvent was distilled off under reduced pressure
10. dissolutionthe obtained syrup crude product was dissolved in 100 ml of dry methanol
11. additionThen, 2 ml of a methanol solution of sodium methoxide (28 wt %) was added
12. filtrationfiltered through Celite®
13. customto remove the precipitate
14. concentrationThe filtrate was concentrated under reduced pressure
15. customthe obtained crude product
16. customwas purified by silica gel column chromatography (ethyl acetate: hexane=1:2)

ORD record

ord-5c52a55d707a4408a7aea347843ba0bc

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380834