Formaldehyde → HCID 86748386, compound

Participants

Reaction Conditions

Reaction Steps

1.65 g of 1,6-anhydro-3-bromo-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose ethylene acetal obtained in the above Intermediate Preparation Example 8 (1), was dissolved in 200 ml of dry tetrahydrofuran, and the solution was cooled to -78° C. Then, 5 ml (1.6N) of n-butyl lithium was gradually added thereto, and the mixture was further stirred for 20 minutes. To the obtained reaction mixture, formaldehyde gas was introduced in large excess, and the temperature was raised to room temperature. Termination of the reaction was confirmed by TLC, and then the reaction mixture was filtered through Celite® to remove the precipitate. The filtrate was concentrated under reduced pressure, and the obtained syrup crude product was purified by silica gel column chromatography (ethyl acetate: hexane=1:1) to obtain 0.7 g of 1,6-anhydro-3,4-dideoxy-3-hydroxymethyl-β-D-glycero-hex-3-enopyranos-2-ulose ethylene acetal. The NMR analytical data of this product are as follows.

Provenance & Evidence