Acetone → 1,6-anhydro-beta-D-altropyranose

Participants

Reaction Steps

3.84 g (30.0 mmol) of the compound (2) obtained in step a), 0.76 g (3.0 mmol) of osmium tetroxide, and 7.03 g (60.0 mmol) of N-methyl morpholin-N-oxide were dissolved in a mixed solvent consisting of 8 parts of acetone and 1 part of water, and the resultant solution was kept stirred at room temperature for 13 hours. Then, 81.0 g (643 mmol) of sodium sulfite was added to the reaction system, followed by removing the solvent by distillation under reduced pressure. Further, hot ethanol was added to the residue to wash the residue, followed by filtration and subsequent distillation of the filtrate under reduced pressure so as to remove the ethanol. The residue after the distillation was refined by means of a silica gel column chromatograph. A mixed solvent consisting of methylene chloride and acetone was used as an eluent for the column chromatograph. The mixing ratio of methylene chloride to acetone fell within a range of between 1:2 and 1:4. Finally, the formed product was recrystallized from 2-propanol so as to obtain 4.19 g of 1,6-anhydro-β-D-altropyranose (D-altrosan; compound 3). The product yield was 86.0%. The physical data of the formed product were found to be as follows:

Provenance & Evidence