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Merck
모든 사진(1)

주요 문서

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SMB00504

Sigma-Aldrich

Levoglucosenone

≥95% (GC)

동의어(들):

(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

실험식(Hill 표기법):
C6H6O3
CAS Number:
37112-31-5
Molecular Weight:
126.11
MDL number:
MFCD00191664
UNSPSC 코드:
12352201
PubChem Substance ID:
329825031
NACRES:
NA.25

분석

≥95% (GC)

양식

liquid

저장 온도

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

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일반 설명

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.[1] It can also be synthesized from the acid-treated cellulose and paper via pyrolysis.[2] 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.[3] Magnetic super acid (SO4-2/TiO2-Fe3O4) mediated pyrolysis of cellulose and poplar wood has been proposed for the selective synthesis of LGO.[4]

애플리케이션

Levoglucosenone may be used in the synthesis of the following:
  • various deoxy, keto and branched-chain sugars[1]
  • 4-thio and 4-substituted sugar derivatives[2]
  • natural stereoisomer of serricornin[5]

픽토그램

Exclamation mark
GHS07

신호어

Warning

유해 및 위험 성명서

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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시험 성적서(COA)

Lot/Batch Number
MKCT7123
MKCK7380

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문서 라이브러리 방문

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
Michael-addition reactions of levoglucosenone.
Shafizadeh F, et al.
Carbohydrate Research, 102(1), 217-230 (1982)
Preparation of 1, 6-anhydro-3, 4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and some derivatives thereof.
Shafizadeh F and Chin PPS.
Carbohydrate Research, 58(1), 79-87 (1977)

질문

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