58238-40-7

Upstream product

• 50705-29-8 2-O-acetyl-1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 71856-30-9 dianhydroaltrose 
• 37112-31-5 levoglucosenone 
• 50705-28-7 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 3868-04-0 1,6:3,4-dianhydro-β-D-altropyranose 

Downstream Products

• 39726-36-8 (1R,2S,5R)-6,8-dioxabicyclo[3.2.1]octan-2-ol 
• 58394-31-3 1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose 
• 33647-85-7 isolevoglucosenone 
• 14086-08-9 (R)-2-(2-furyl)-1,2-ethanediol 

Relevant academic research and scientific papers

Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives

High-yielding epoxidation conditions for the cellulose pyrolysis product (?)-levoglucosenone (LGO) and 3-aryl derivatives of LGO have been developed. The reaction of LGO with hydrogen peroxide/base is known to give a Baeyer-Villiger reaction, however, it was found that the reactions of LGO or derivatives with tert-butylhydroperoxide/base affords solely epoxides through the Weitz-Scheffer reaction. A critical parameter in the successful isolation of the epoxide from LGO was to avoid all contact with water or alcohols during the reaction and workup. The epoxide products were reacted under Wharton conditions affording allylic alcohols and subsequent oxidation led to isolevoglucosenone or 3-arylisolevoglucosenone derivatives. Previously unreported reactions on isolevoglucosenone were then investigated.

The conversion of levoglucosenone into isolevoglucosenone

Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.