Levoglucosan

Base Information

• Chemical Name: Levoglucosan
• CAS No.: 498-07-7
• Deprecated CAS: 112602-30-9
• Molecular Formula: C6H10O5
• Molecular Weight: 162.142
• Hs Code.: 29400000
• European Community (EC) Number: 207-855-0
• UNII: 5132N17FSD
• Nikkaji Number: J12.571G
• Wikipedia: Levoglucosan
• Wikidata: Q6535767
• Metabolomics Workbench ID: 37345
• ChEMBL ID: CHEMBL3138649
• Mol file: 498-07-7.mol

Synonyms:1,6-anhydro-beta-D-glucopyranose;1,6-anhydro-beta-glucopyranose;levoglucosan

Chemical Property of Levoglucosan

Chemical Property:

• Vapor Pressure: 1.81E-07mmHg at 25°C
• Melting Point: 182-184 °C(lit.)
• Refractive Index: -66.5 ° (C=2, H2O)
• Boiling Point: 383.754 °C at 760 mmHg
• PKA: 13.40±0.60(Predicted)
• Flash Point: 185.888 °C
• PSA: 79.15000
• Density: 1.689 g/cm³
• LogP: -2.17580
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Sparingly)
• Water Solubility.: Soluble in Ethanol and Water.
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 161

Purity/Quality:

99% ^*data from raw suppliers

Levoglucosan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

Useful:

• Canonical SMILES: C1C2C(C(C(C(O1)O2)O)O)O
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)O)O)O
• Uses: 1,6-Anhydro-β-D-glucose is an useful carbohydrate synthon pharmaceutical intermediate. 1,6-Anhydro-beta-D-glucopyranose is used for the preparation of biologically important and structurally diverse products such as rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, macrolide antibiotics and modified sugars. It is used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. It aids in the production of bioethanol.

Technology Process of Levoglucosan

There total 122 articles about Levoglucosan 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: 51.5%

β-D-glucose (492-61-5) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + levoglucosan (498-07-7)

Guidance literature:

With sulfonic acid functionalized carbon coated on acid activated red mud; In water; dimethyl sulfoxide; at 180 ℃; for 0.5h; Reagent/catalyst; Temperature; Microwave irradiation;

DOI:10.1016/j.apcata.2021.118237

Reference yield: 44.0%

cellulose (9004-34-6) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + formic acid (64-18-6) + β-D-glucose (492-61-5) + 5-ketohexanoic acid (3128-06-1) + levoglucosan (498-07-7)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 190 ℃; for 0.166667h; Solvent; Temperature; Time; Catalytic behavior;

DOI:10.1002/cctc.201402299

Reference yield: 10.0%

13C-C1-glucopyranose (40010-55-7,40010-56-8,56746-22-6,60821-16-1,60821-17-2,60821-20-7,60821-21-8) → levoglucosan (498-07-7)

Guidance literature:

With sulfuric acid; In water; at 130 ℃; for 0.0166667h; Green chemistry;

DOI:10.1021/cs401160y

upstream raw materials:

formic acid

D-glucose

β-D-glucose

(2,4,6-tribromo-phenyl)-β-D-glucopyranoside

Downstream raw materials:

1,6-anhydro-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranose

1,6-anhydro-4-O-(2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)-β-D-galactopyranose

1,6-anhydro-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranose

3,4-di-O-acetyl-1,6-anhydro-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranose

Refernces

• 1、 Singh,Brown. "-". . p. 1791. Retrieved 1970.
• 2、 Das, Bikashbindu,Mohanty, Kaustubha. "Sulfonic acid-functionalized carbon coated red mud as an efficient catalyst for the direct production of 5-HMF from D-glucose under microwave irradiation". . . Retrieved 2021.
• 3、 Bacik, John-Paul,Klesmith, Justin R.,Whitehead, Timothy A.,Jarboe, Laura R.,Unkefer, Clifford J.,Mark, Brian L.,Michalczyk, Ryszard. "Producing Glucose 6-phosphate from cellulosic biomass: Structural insights into levoglucosan bioconversion". . p. 26638 - 26648. Retrieved 2015.
• 4、 Takagaki, Atsushi,Ebitani, Kohki. "Glucose to value-added chemicals: Anhydroglucose formation by selective dehydration over solid acid catalysts". . p. 650 - 651. Retrieved 2009.
• 5、 Locas, Carolina Perez,Yaylayan, Varoujan A.. "Isotope labeling studies on the formation of 5-(hydroxymethyl)-2- furaldehyde (HMF) from sucrose by pyrolysis-GC/MS". . p. 6717 - 6723. Retrieved 2008.
• 6、 Ghosh, Arpa,Brown, Robert C.,Bai, Xianglan. "Production of solubilized carbohydrate from cellulose using non-catalytic, supercritical depolymerization in polar aprotic solvents". . p. 1023 - 1031. Retrieved 2016.
• 7、 Cerny, Miloslav,Trnka, Tomas,Redlich, Hartmut. "Praktische Darstellung von 1,6-Anhydro-β-D-glucopyranose durch Vakuumpyrolyse von Staerke. Kriterien fuer den Bau eines Stahlreaktors". . p. 349 - 353. Retrieved 1988.
• 8、 Faba, Laura,Garcés, Diego,Díaz, Eva,Ordó?ez, Salvador. "Carbon Materials as Phase-Transfer Promoters for Obtaining 5-Hydroxymethylfurfural from Cellulose in a Biphasic System". . p. 3769 - 3777. Retrieved 2019/07/04.