Potassium Iodide → HCID 9937956, compound

Participants

Reaction Steps

Methyl 1,2,3,4-tetra-O-pivaloyl-β-D-glucopyranuronate (2.72 g, 5 mmol) in acetonitrile (10 cm3) was heated and stirred at gentle reflux under argon with potassium iodide (1.66 g, 10 mmol) and boron trifluoride diethyl etherate (2.50cm3). After 1 h the dark mixture was cooled, then 10% aq. sodium thiosulfate (25 cm3) and saturated aqueous sodium bicarbonate (NaHCO3) (25 cm3) were added and the product was extracted using ethyl acetate (50 cm3+20 cm3). The combined organic phases were washed with further NaHCO3, water and brine, then dried over anhydrous Na2SO4 and evaporated to an orange gum (2.8 g). Triuration with ethanol gave a crystalline product; evaporation of the mother liquors, followed by chromatography on silica gel, eluting with 10% ethyl acetate in hexane, afforded further product of equal purity; combined yield, 1.89 g (66%), m.p. 98-100° C.; δH (220 MHz, CDC13) 1.10-1.30 (27H, 3s), 3.73 (3H, s), 4.26 (1H, dd), 4.35 (1H, d), 5.22, 5.61 (2H, 2t) and 7.04 (1H, d).

Provenance & Evidence