3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

Base Information

• Chemical Name: 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid
• CAS No.: 216581-47-4
• Molecular Formula: C14H12O5
• Molecular Weight: 260.246
• DSSTox Substance ID: DTXSID40431879
• Wikidata: Q82245887
• ChEMBL ID: CHEMBL485159
• Mol file: 216581-47-4.mol

Synonyms:216581-47-4;3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid;6-methyl-4-oxo-3-phenylmethoxypyran-2-carboxylic acid;2-Carboxy-3-benzyloxy-6-methyl-pyran-4(1H)-one;SCHEMBL338697;SCHEMBL622608;CHEMBL485159;DTXSID40431879;WYDDQRFWOUARKA-UHFFFAOYSA-N;MFCD26386738;AKOS025296223;SB13455;PS-16740;CS-0439135;P20316

Chemical Property of 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

Chemical Property:

• PSA: 76.74000
• LogP: 2.22540
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 260.06847348
• Heavy Atom Count: 19
• Complexity: 441

Purity/Quality:

≥99.0% ^*data from raw suppliers

3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylicacid 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)C(=C(O1)C(=O)O)OCC2=CC=CC=C2

Technology Process of 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

There total 7 articles about 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid 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: 85.0%

2-formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one (216581-46-3) → 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (216581-47-4)

Guidance literature:

With sodium chlorite; aminosulfonic acid; In water; acetone; at 25 ℃; for 1h;

DOI:10.1016/S0968-0896(00)00273-X

Reference yield: 73.0%

2-Hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one (216581-77-0) → 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (216581-47-4)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium iodide; In dichloromethane; water; at 7 ℃; for 3h; Cooling with ice;

DOI:10.1021/acs.jmedchem.8b01363

Reference yield:

allomaltol (644-46-2) → 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (216581-47-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / aq. NaOH / 12 h / 25 °C

2: 80 percent / aq. NaOH / methanol / 12 h / Heating

3: 87.7 percent / Et₃N; SO₃*pyridine / CHCl₃; dimethylsulfoxide / 12 h / 25 °C

4: 85 percent / NaClO₂; NH₂SO₃H / acetone; H₂O / 1 h / 25 °C

With sodium hydroxide; sodium chlorite; pyridine-SO₃ complex; aminosulfonic acid; triethylamine; In methanol; chloroform; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0968-0896(00)00273-X

upstream raw materials:

2-formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

allomaltol

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

chlorokojic acid

Downstream raw materials:

3-(benzyloxy)-N,N-diethyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide

1,6-dimethyl-3-benzyloxy-pyridin-4(1H)-one-2-carboxy-(N-methyl)-amide

3-(benzyloxy)-6-methyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid

C₁₄H₁₂FNO₄

Refernces

• 1、 Credille, Cy V.,Dick, Benjamin L.,Morrison, Christine N.,Stokes, Ryjul W.,Adamek, Rebecca N.,Wu, Nicholas C.,Wilson, Ian A.,Cohen, Seth M.. "Structure-Activity Relationships in Metal-Binding Pharmacophores for Influenza Endonuclease". . p. 10206 - 10217. Retrieved 2018/11/23.
• 2、 -. "ANTIVIRAL COMPOUNDS". Page/Page column 115-116. . Retrieved 2012/08/29.