Hydrochloric Acid → HCID 178476616, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.682 g (1.73 mM) of 2-cyano-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation XV, and 1.24 g (6.05 mM) of azidotrimethyltin in 10 ml of toluene is prepared and this mixture is stirred at 70° C. for 7 days. After cooling, the reaction medium is poured onto a mixture of water and ethyl acetate and brought to pH 1 by addition of an N hydrochloric acid solution. The aqueous phase is extracted, brought to pH 5 by addition of a dilute sodium hydroxide solution and extracted with ethyl acetate. This organic phase is separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol mixture (95/5;v/v). The expected compound is thus obtained in the form of a white foam (yield=30%).

Provenance & Evidence