Levoglucosenone

Base Information

• Chemical Name: Levoglucosenone
• CAS No.: 37112-31-5
• Molecular Formula: C6H6 O3
• Molecular Weight: 126.112
• Hs Code.: 2932999099
• UNII: B7N23SN1LB
• Nikkaji Number: J405.523C
• Wikipedia: Levoglucosenone
• Wikidata: Q27114054
• Metabolomics Workbench ID: 54314
• ChEMBL ID: CHEMBL4126941
• Mol file: 37112-31-5.mol

Synonyms:1,6-anhydro-3,4-dideoxy-beta-D-glycero-hex-3-enopyran-2-ulose;1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose;levoglucosenone

Chemical Property of Levoglucosenone

Chemical Property:

• Vapor Pressure: 0.0173mmHg at 25°C
• Refractive Index: nD25 1.5084
• Boiling Point: 254.4°Cat760mmHg
• Flash Point: 98.2°C
• PSA: 35.53000
• Density: 1.329g/cm³
• LogP: -0.13320
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 126.031694049
• Heavy Atom Count: 9
• Complexity: 173

Purity/Quality:

97% ^*data from raw suppliers

Levoglucosenone ^*data from reagent suppliers

Safty Information:

• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC(=O)C(O1)O2
• Isomeric SMILES: C1[C@@H]2C=CC(=O)[C@H](O1)O2
• General Description: Levoglucosenone is a chiral bicyclic compound with the chemical name 6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, (1S)-, and serves as a valuable synthetic intermediate for optically active compounds. This study demonstrated its efficient synthesis via lipase-mediated kinetic resolution, enabling the production of both enantiomers from acrolein dimer through a multi-step process involving reduction, acetalization, oxidation, and enzymatic resolution. The successful enantioselective synthesis highlights its utility as a versatile chiral building block in organic chemistry.

Technology Process of Levoglucosenone

There total 22 articles about Levoglucosenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.3%

cellulose (9004-34-6) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + levoglucosenone (37112-31-5)

Guidance literature:

With sulfuric acid; In diethylene glycol dimethyl ether; at 210 ℃; for 45h; under 51716.2 Torr; Solvent; Catalytic behavior; Autoclave; Inert atmosphere;

DOI:10.1039/c7gc01688c

Reference yield: 39.7%

cellulose (9004-34-6) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + levoglucosenone (37112-31-5)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; at 210 ℃; for 47h; under 51716.2 Torr; Solvent; Autoclave; Inert atmosphere;

DOI:10.1039/c7gc01688c

Reference yield: 36.6%

methyl 4-O-methyl-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside (112988-85-9) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + α-D-glucofuranose cyclic 1,2:3,5-bisborate (1012081-04-7) + levoglucosenone (37112-31-5)

Guidance literature:

With sulfuric acid/sulfolane; at 200 ℃; for 0.0333333h;

DOI:10.1016/j.carres.2007.11.004

upstream raw materials:

methyl 4-O-methyl-β-D-glucopyranoside

methyl 4-O-methyl-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside

cellulose

levoglucosan

Downstream raw materials:

1,6-anhydro-2,3-dideoxy-4-methoxy-β-D-erythro-hexopyranos-2-ulose

1,6-anhydro-4-S-cyclohexyl-3-deoxy-4-thio-β-D-erythro-hexopyranos-2-ulose

(1S)-(1α,2α,3β,6β,8α,9α)-5,13,14-trioxatetracyclo<7.3.1.1^3,6.0^2,8>tetradeca-10-en-7,12-dione

(1R)-(1α,2β,3α,6α,8β,9α)-5,13,14-trioxatetracyclo<7.3.1.1^3,6.0^2,8>tetradeca-10-en-7,12-dione

Refernces

Lipase-Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer

10.1002/1615-4169(200108)343:6/7<618::AID-ADSC618>3.0.CO;2-E

The research focuses on the synthesis of both enantiomers of levoglucosenone from acrolein dimer using lipase-mediated kinetic hydrolysis. The purpose of this study was to develop an efficient method for the synthesis of levoglucosenone, a chiral building block with high chemical potential, which is utilized in the construction of various optically active compounds. The researchers concluded that they had successfully developed a new route to racemic levoglucosenone and its resolution into both enantiomers of enantiopure levoglucosenone. Key chemicals used in the process included acrolein dimer, sodium borohydride, vinyl acetate, p-toluenesulfonic acid, m-chloroperbenzoic acid, o-iodoxybenzoic acid, and various lipases for the enzymatic resolution steps. The synthesis involved several steps, including reduction, oxidative acetalization, Swern oxidation, and dehydrogenation, ultimately leading to the desired enantiomers of levoglucosenone.

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