SMB00504
Levoglucosenone
≥95% (GC)
Synonym(s):
(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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About This Item
Empirical Formula (Hill Notation):
C6H6O3
CAS Number:
Molecular Weight:
126.11
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352201
MDL number:
assay
≥95% (GC)
form
liquid
storage temp.
2-8°C
SMILES string
[H][C@]1(C=CC2=O)CO[C@]2([H])O1
InChI
1S/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4-,6+/m0/s1
InChI key
HITOXZPZGPXYHY-UJURSFKZSA-N
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.
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
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Some reactions of levoglucosenone.
Shafizadeh F, et al.
Carbohydrate Research, 71(1), 169-191 (1979)
A stereoselective synthesis of ?natural?(4S, 6S, 7S)-serricornin, the sex pheromone of cigarette bettle, from levoglucosenone.
Mori M, et al.
Tetrahedron Letters, 23(44), 4593-4596 (1982)
Qiang Lu et al.
Bioresource technology, 171, 10-15 (2014-09-01)
Magnetic superacid (SO4(2-)/TiO2-Fe3O4) was prepared for catalytic fast pyrolysis of cellulose and poplar wood to produce levoglucosenone (LGO). Its catalytic activity was evaluated via pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) experiments, and compared with the non-magnetic SO4(2-)/TiO2, phosphoric acid (H3PO4) and sulfur
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SMB00504-10MG | 04061833052549 |