Efficient levoglucosenone production

Levoglucosenone

Levoglucosenone is a highly dehydrated sugar that has been used in the preparation of chiral synthons such as (–)-y-multistriatin and (+)-Prelog—Djerassi lactonic acid.

Negative-form is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Known as a pyrolytic product of cellulose, which is very useful as a chiral source for synthesizing natural products.

Levoglucosenone

Density 1.29 g/mL
Boiling Point 57-57.5 °C / 0.5 mm
CAS No:
37112-31-5
Synonyms:

1,6-Anhydro-3,4-dideoxy-a-D-glycero-hex-3-enopyranose-2-ulose
(1S,5R)-6,8-Dioxobicyclo[3.2.1]oct-2-en-4-one
Solubility: Soluble in Chloroform
Physical Appearance: Colorless to Yellow Oil
Chemical Formula:
C6H6O3
Molecular Weight:
126.11
References:

1. Shafizadeh F, Furneaux R, Stevenson T, Carbohydr. Res. 1979 and Essig, M.G., et al.: Carbohydr. Res., 156, 225 (1986)

also Taniguchi, T., et al.: Synlett, 971 (1996),

Efficient levoglucosenone production

Shinji Kudo ,  et al, Green Chem., 2011,13, 3306-3311

DOI: 10.1039/C1GC15975E

http://pubs.rsc.org/en/Content/ArticleLanding/2011/GC/c1gc15975e    COPY PASTE LINK

Graphical abstract: Efficient levoglucosenone production by catalytic pyrolysis of cellulose mixed with ionic liquid
Levoglucosenone is a synthetically valuable and versatile compound that is present as a minor product of cellulose pyrolysis. Here, the paper  reports the catalytic pyrolysis of cellulose by mixing with 1-butyl-2,3-dimethylimidazolium triflate ionic liquid (IL), forming levoglucosenone in high yield. The catalysis of the IL was selectively directed to form levoglucosenone, while the low content of IL (50%) effectively prevented formation of char, leading to a yield near 20% even at 250 °C. The thermally stable IL could be fully recovered from the mixture pyrolyzed up to 300 °C and reutilized for pyrolysis.

Levoglucosenone

See papers on levoglucosenone:
(1S,5R)-6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one
M.S.Miftakhov, et al.
Levoglucosenone: the properties, reactions, and use in fine organic synthesis
Russ.Chem.Rev., 1994, 63 (10), 869-882

Herdewijn P, et al.
3′-substituted 2′,3′-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents
J.Med.Chem., 1987, 30(8), 1270-1278

M.Jung and M.Kiankarimi
Synthesis of Methylene-Expanded 2′,3′-Dideoxyribonucleosides
J.Org.Chem., 1998, 63 (23), 8133-8144

http://levoglucosenone.com/derivatives/     COPY PASTE LINK

 

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