Triphenylphosphine → 5-[(2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl)oxy]-1H-indole-1-carboxylic Acid 1,1-dimethylethyl Ester

Participants

Reaction Conditions

Reaction Steps

A solution of 1.75 g (7.51 mM) of 5-hydroxy-1H-indole-1-carboxylic acid tert-butyl ester in 25 ml of THF, 2.73 g (13.5 mM) of diisopropylazodicarboxylate and 3.54 g (13.5 mM) of triphenylphosphine are added to a solution of 2.85 g (9.75 mM) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranose in 50 ml of THF. The reaction mixture is stirred at 45° C. for 3 hours and then concentrated under reduced pressure. The evaporation residue is dissolved in ethyl acetate and the organic phase is washed with a 1N solution of sodium hydroxide, and then with a concentrated aqueous solution of ammonium chloride. The organic phase is subsequently dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by C18-grafted silica chromatography, elution being carried out with an acetonitrile/water mixture (7/3; v/v). The desired product is obtained in the form of a pale yellow solid with a yield of 11%.

Provenance & Evidence