Dimethyl Sulfoxide → 5-(phenylsulfonyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

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Reaction Conditions

Reaction Steps

0.495 g (1 mM) of 5-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylo-pyranoside, 4 ml of DMSO, 0.025 g (0.05 mM) of benzene/copper trifluoro-methanesulfonate complex, 0.196 g (1.2 mM) of phenyl sulfinate and 0.0088 g (0.1 mM) of N,N′-dimethylethylenediamine are mixed under an argon atmosphere in a reactor adapted for microwaves. The mixture is heated at 130° C. for 3 hours by microwaves. Water is added to the cooled reaction mixture and extraction is carried out with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a toluene/acetone mixture (9/1; v/v) as the eluent to give the expected product in the form of a white solid with a yield of 43%.

Provenance & Evidence