(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 131727790, compound

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Reaction Steps

To a mixture of 20.0 g of D-glucose, 3.4 g of 4-(N,N-dimethylamino)pyridine, 68.0 g of TEA and 440 g of THF, a solution of 86.0 g of cis-1,2-cyclohexanedicarboxylic anhydride and 88 g of THF was added with stirring at room temperature, then the added mixture was stirred for 3 days. After the stirring, the solvent was removed from the resulting mixture under reduced pressure. To the concentrate, 600 g of chloroform and 300 g of ion-exchanged water was added, and was neutralized with hydrochloric acid. The neutralized organic layer was separated, washed with ion-exchanged water, and dried with anhydrous magnesium sulfate. Then the solvent was removed from the dried organic layer to obtain 160.1 g of crude pentakis-D-glucose (2-carboxycyclohexyl)carboxylate (abbreviated to “GLUCHA”).

Provenance & Evidence