Preparation of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and some derivatives thereof

1,6-Anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) was prepared on a laboratory scale by pyrolysis of H₃PO₄-treated, Kraft waste-paper. The aldehyde components of the pyrolyzate were removed by reaction with 5,5-dimethyl-1,3-cyclohexanedione (dimedone), and levoglucosenone was obtained in 3.3% yield by distillation of the remaining material. A variety of deoxy, keto, and branched-chain sugars was obtained by reduction of levoglucosenone, and by its reaction with Grignard reagents under different conditions.