Methanol → 1,6-anhydro-3,4-dideoxy-beta-D-threo-hex-3-enopyranose

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Reaction Steps

2.42 g (63.8 mmol) of lithium almunium hydride was added to 200 ml of dry ether to prepare a hydride solution, followed by adding dropwise a solution prepared by dissolving 7.98 g (63.3 mmol) of levoglucosenone in 130 ml of dry ether into the hydride solution while cooling the hydride solution in an ice water bath. After completion of the addition, the resultant solution was kept stirred at room temperature for an hour, followed by further adding dropwise 4.60 g (256 mmol) of water to the solution. Then, methanol was added to the reaction mixture, followed by removing the insoluble components by means of filtration. Further, the solvent was removed from the filtrate by means of distillation under reduced pressure, followed by refining the residue by means of a silica gel column chromatograph. A mixed solvent consisting of hexane and diethyl ether was used as an eluent for the column chromatograph. The mixing ratio of hexane to diethyl ether fell within a range of between 1:1 and 1:2. Finally, the formed product was recrystallized from a mixed solvent consisting of 4 parts of hexane and 1 part of diethyl ether so as to obtain 5.70 g of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose (compound 2). The product yield was 70.3%. The physical data of the formed product were found to be as follows:

Provenance & Evidence