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:

98%,99%, ^*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
• Uses: (-)-Form Levoglucosenone is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Known as a pyrolytic product of cellulose, its very useful as a chiral source for synthesizing natural products. useful carbohydrate synthon Chiral building block in organic synthesis.

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,2R,5R)-2-Phenyl-6,8-dioxabicyclo<3.2.1>octan-4-on

(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

Refernces

• 1、 Wang, Zhi,Lu, Qiang,Zhu, Xi-Feng,Zhang, Ying. "Catalytic fast pyrolysis of cellulose to prepare levoglucosenone using sulfated zirconia". . p. 79 - 84. Retrieved 2011.
• 2、 Arora, Jyotsna S.,Ansari, Khursheed B.,Chew, Jia Wei,Dauenhauer, Paul J.,Mushrif, Samir H.. "Unravelling the catalytic influence of naturally occurring salts on biomass pyrolysis chemistry using glucose as a model compound: A combined experimental and DFT study". . p. 3504 - 3524. Retrieved 2019.
• 3、 Zhao, Pingping,Cui, Hongyou,Zhang, Yunyun,Zhang, Yuan,Wang, Yong,Zhang, Yali,Xie, Yujiao,Yi, Weiming. "Synergetic Effect of Br?nsted/Lewis Acid Sites and Water on the Catalytic Dehydration of Glucose to 5-Hydroxymethylfurfural by Heteropolyacid-Based Ionic Hybrids". . p. 824 - 832. Retrieved 2018/10/31.