Iodine → 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one, 3-iodo-, (1S,5R)-

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Reaction Steps

150 ml of a dry pyridine-carbon tetrachloride (1:1) solution containing 40 g of iodine, was gradually added at 0° C. to 150 ml of a dry pyridine-carbon tetrachloride (1:1) solution containing 5 g of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (disclosed in U.S. Pat. No. 3,926,947) under an inert atmosphere of nitrogen gas. The mixture was stirred at room temperature for two hours. Then, disappearance of the starting material was confirmed by thin layer chromatography, and 200 ml of ethyl acetate was added thereto. The mixture was washed twice with 200 ml of a saturated sodium chloride aqueous solution and once with 200 ml of 20% sodium thiosulfate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained syrup crude product was purified by silica gel column chromatography (ethyl acetate: hexane=1:3) to obtain 6.1 g of the desired product (Intermediate No. 5) as slightly yellow crystals. The NMR analytical data and physical data of this product are as follows.

Provenance & Evidence