Water → Phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside

To a solution of phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside (3) (1.09 g, 2.00 mmol) in DMF (10 ml) was added sodium hydride (60% in oil, 96 mg, 2.40 mmol), and the resulting mixture was stirred at room temperature for 15 min. The reaction mixture was cooled to 0° C. and 4-azido-3-chlorobenzyl bromide (592 mg, 2.40 mmol) was added, which was followed by stirring at room temperature for 4 hr. Water (30 ml) was added and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to give phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside (4) (1.33 g, yield 94%) as slightly yellow crystals.

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringby stirring at room temperature for 4 hr
3. extractionthe mixture was extracted twice with ethyl acetate
4. washwashed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue obtained
8. customwas purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

ORD record

ord-baf9956c10ff45dd9d3ad2545077ee52

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998595