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SMB00504 Sigma-Aldrich

Levoglucosenone

≥95% (GC)

Synonym: (1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose, 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one

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Properties

Related Categories Biochemicals and Reagents, Carbohydrates, Carbohydrates A to Z, Carbohydrates H-L, Monosaccharide More...
InChI Key   HITOXZPZGPXYHY-UJURSFKZSA-N
assay   ≥95% (GC)
form   liquid
storage temp.   2-8°C

Description

Packaging

10 mg in glass bottle

Application

Levoglucosenone may be used in the synthesis of the following:
• various deoxy, keto and branched-chain sugars
• 4-thio and 4-substituted sugar derivatives
• natural stereoisomer of serricornin

General description

In the laboratory, levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose, LGO) can be synthesized from H3PO4-treated, Kraft waste-paper via pyrolysis. It can also be synthesized from the acid-treated cellulose and paper via pyrolysis. It undergoes Michael-addition reaction with diethyl malonate, ethyl cyanoacetate, 2-nitropropane and 2-methylcyclohexanone in the presence of various catalysts to afford 4-substituted levoglucosenone derivatives having the D-erythro configuration. Magnetic super acid (SO4-2/TiO2-Fe3O4) mediated pyrolysis of cellulose and poplar wood has been proposed for the selective synthesis of LGO.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
RTECS 
JG7020000

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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