3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

Base Information

• Chemical Name: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid
• CAS No.: 119736-16-2
• Molecular Formula: C13H10O5
• Molecular Weight: 246.219
• Mol file: 119736-16-2.mol

Synonyms:2-carboxy-3-benzyloxy-pyran-4(1H)-one;4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic Acid;3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid;2-carboxy-3-benzyloxypyran-4(1H)-one;3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid;3-(benzyloxy)-4-oxopyran-2-carboxylic acid;3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylicacid;BPCA;

Chemical Property of 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

Chemical Property:

• Boiling Point: 487.5±45.0 °C(Predicted)
• PKA: 2.00±0.20(Predicted)
• PSA: 76.74000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 1.91700
• Storage Temp.: 2-8°C

Purity/Quality:

4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: There are a variety of preclinical, clinical, and marketed new drugs that contain 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid fragments. As shown in the figure below, several types of drug molecules, as well as the marketed drugs such as dulutevir (GSK1349572) and baloxavir (Baloxavir) contain this important structural fragment. 4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylic Acid is an intermediate in the synthesis of Dolutegravir (D528800), a second generation HIV-1 integrase strand transfer inhibitor.

Technology Process of 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

There total 23 articles about 3-(Benzyloxy)-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: 97.0%

3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde (500371-01-7) → 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester (119736-16-2)

Guidance literature:

With sodium hypochlorite; aminosulfonic acid; In water; acetone; at 20 ℃; for 2h;

DOI:10.1007/s00044-012-0229-1

Reference yield: 91.0%

C15H14O4 → 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester (119736-16-2)

Guidance literature:

C₁₅H₁₄O₄; With sodium periodate; In water; ethyl acetate; at 20 ℃;

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield: 89.0%

C21H18O4 → 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester (119736-16-2)

Guidance literature:

C₂₁H₁₈O₄; With sodium periodate; In water; toluene; at 20 ℃;

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; In water; toluene;

upstream raw materials:

2-(hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one

3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde

Maltol

3-O-benzylmaltol

Downstream raw materials:

1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid

1-[2,2-bis(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridine carboxylic acid

C₁₆H₁₅NO₄

N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(3-(benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxamide)

Refernces

• 1、 -. "Preparation method of intermediate of antiviral drug". . . Retrieved 2021/06/22.
• 2、 -. "Synthesis method of 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid". Paragraph 0043; 0087-0098. . Retrieved 2021/03/31.