Isolevoglucosenone

Base Information

• Chemical Name: Isolevoglucosenone
• CAS No.: 33647-85-7
• Molecular Formula: C6H6 O3
• Molecular Weight: 126.112
• Hs Code.: 2932999099
• Metabolomics Workbench ID: 54636
• Nikkaji Number: J773.823D
• Wikidata: Q27115001
• Mol file: 33647-85-7.mol

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

Chemical Property of Isolevoglucosenone

Chemical Property:

• PSA: 35.53000
• LogP: -0.13320
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(=O)C=CC(O1)O2
• Isomeric SMILES: C1[C@@H]2C(=O)C=C[C@H](O1)O2

Technology Process of Isolevoglucosenone

There total 51 articles about Isolevoglucosenone 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: 89.0%

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose (58394-31-3,52630-80-5,52630-81-6) → isolevoglucosenone (33647-85-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 6h; Further Variations:; Reagents; Product distribution;

DOI:10.1081/CAR-120003745

Reference yield: 84.0%

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose (307991-11-3,52630-80-5,52630-81-6) → (-)-(1S,5S)-Isolevoglucosenone (33647-85-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2000-7099

Reference yield: 82.0%

1,6-anhydro-2,3-dideoxy-β-threo-hex-2-enopyranose (58394-32-4,52630-80-5,52630-81-6) → isolevoglucosenone (33647-85-7)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2000-7099

upstream raw materials:

1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose

6-hydroxy-2-hydroxymethyl-6H-pyran-3-one

(S)-1-(α-furyl)-1,2-ethanediol

(furan-2-yl)ethylene

Downstream raw materials:

1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose

3,4-isopropylidenedioxy-Δ¹-pyrroline-1-oxide

(3S,4R)-3,4-O-isopropylidenedioxy-1-pyrroline-N-oxide

C₁₃H₁₇NO₆

Refernces

• 1、 Ma, Xinghua,Liu, Xin,Yates, Patrick,Raverty, Warwick,Banwell, Martin G.,Ma, Chenxi,Willis, Anthony C.,Carr, Paul D.. "Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone". . p. 5000 - 5011. Retrieved 2018/06/20.
• 2、 Biktagirov,Faizullina,Salikhov,Safarov,Valeev. "Synthesis of α-bromoisolevoglucosenone and its cyclopenta annulation". . p. 1317 - 1322. Retrieved 2015/01/08.