Sodium Iodide → 5-iodo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

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Reaction Conditions

Reaction Steps

1.34 g (3 mM) of 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-α-D-xylo-pyranoside, 10 ml of dioxane, 0.057 g (0.3 mM) of copper(I) iodide, 0.899 g (6 mM) of sodium iodide and 0.085 g (0.6 mM) of (1R,2R)—N,N′-dimethyl-1,2-cyclohexanediamine are mixed under an argon atmosphere in a reactor adapted for microwaves and the mixture is heated for 3 h 30 min at 130° C. 100 ml of water are added to the cooled reaction mixture and extraction is then carried out with ethyl acetate. The organic phase is washed with 1 N sodium thiosulfate solution and with water, dried over sodium sulfate and then concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a toluene/acetone mixture (1/1; v/v) as the eluent to give the expected product in the form of a white solid with a yield of 85%.

Provenance & Evidence