Toluene → 4-Chloro-2-(5-isoxazolyl)-5-methylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Temperature

80 °C

A mixture of 0.8 g (5.87 mmol) of zinc chloride, 2 g of 13× molecular sieve, 2 g (5.6 mmol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1 g (4.77 mmol) of 4-chloro-2-(5-isoxazolyl)-5-methylphenol, 1 g (5.7 mmol) of silver imidazolate, 5 ml of toluene and 5 ml of acetonitrile is prepared. The mixture is kept stirred at 80° C. for 90 minutes and then cooled and filtered. The residual solid is rinsed on the filter with methanol and the combined filtrates are concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel, elution being carried out using a dichloromethane/ethyl acetate mixture (9/1; v/v). The pure fraction is crystallized from ethyl ether. The expected compound is thus obtained in the form of a white solid with a yield of 10%.

1. customis prepared
2. temperaturecooled
3. filtrationfiltered
4. washThe residual solid is rinsed on the
5. filtrationfilter with methanol
6. concentrationthe combined filtrates are concentrated under reduced pressure
7. customThe crude product obtained
8. customis purified by chromatography on silica gel, elution
9. customThe pure fraction is crystallized from ethyl ether

ORD record

ord-11ee1b2f8c374600a95f8a22fe0cc99f

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013010B2