ChemicalBook > CAS DataBase List > 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

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

Product Name: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid
CAS No.: 119736-16-2
Chemical Name: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid
Synonyms: BPCA;Baloxavir Impurity 31;Baloxavixate Impurity 4;Baloxavir Marboxil Impurity 2;4-oxo-3-phenylmethoxypyran-2-carboxylic acid;3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid;4-Oxo-3-(benzyloxy)-4H-pyran-2-carboxylic acid;Pinacol 1 - (1-ethoxyethyl) - 4-pyrazole borate;4-Oxo-3-(phenylmethoxy)-4H-pyran-2-carboxylic acid;4H-Pyran-2-carboxylic acid, 4-oxo-3-(phenylmethoxy)-
CBNumber: CB42718404
Molecular Formula: C13H10O5
Formula Weight: 246.22
MOL File: 119736-16-2.mol

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

Boiling point:: 487.5±45.0 °C(Predicted)
Density: 1.39±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
pka: 2.00±0.20(Predicted)
form: Solid
color: White
InChI: InChI=1S/C13H10O5/c14-10-6-7-17-12(13(15)16)11(10)18-8-9-4-2-1-3-5-9/h1-7H,8H2,(H,15,16)
InChIKey: KJSJBKBZMGSIPT-UHFFFAOYSA-N
SMILES: C1(C(O)=O)OC=CC(=O)C=1OCC1=CC=CC=C1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: O858450
Product name: 4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylicAcid
Packaging: 250mg
Price: $580
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB167699
Product name: 3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid
Packaging: 100g
Price: $700
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB167699
Product name: 3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid
Packaging: 25g
Price: $300
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM1554642
Product name: 3-(BENZYLOXY)-4-OXO-4H-PYRAN-2-CARBOXYLIC ACID
Purity: 95.00%
Packaging: 5MG
Price: $500.92
Updated: 2021/12/16

AK Scientific

Product number: 7515CZ
Product name: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylicacid
Packaging: 5g
Price: $119
Updated: 2021/12/16

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3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid Chemical Properties,Usage,Production

Uses

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.

Pharmaceutical Applications

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.

Synthesis

Add 2-(hydroxymethyl)-3-(benzyloxy)-4H-pyran-4-one (Compound IV) 39.8Kg, dichloromethane (340L) and water (170L) to the reaction kettle to start stirring. Then add sodium bicarbonate (77Kg), sodium bromide (1.6Kg) and 2,2,6,6-tetramethylpiperidine-nitrogen-oxide (TEMPO) (2.3Kg), cool to 5℃, drop Add 10% sodium hypochlorite (340Kg). After the dropwise addition, stir at 5°C for 1 hour. The reaction is completed. Add 30% aqueous sodium thiosulfate solution (242L) and stir for 1 h. Add concentrated hydrochloric acid to adjust pH=4, separate the organic phase, extract the aqueous phase twice with dichloromethane (120L), combine the organic phases, and concentrate under reduced pressure to obtain the crude product. The crude product was recrystallized from acetonitrile to obtain 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid (Compound VI) 32.4Kg, purity 99%, yield 77%. LC-MS: [M+H] + = 247.06, [M] + = 245.05; 1 H NMR (DMSO-d 6 ) δ8.00 (d, J = 5.6 Hz, 1H), 7.17 (s, 5H), 6.34 (d, J = 5.7 Hz, 1H), 4.91 (s, 2H), 2.30 (s, 1H).

References

[1] Patent: US9133216, 2015, B2. Location in patent: Page/Page column 16; 19
[2] Patent: WO2010/11816, 2010, A1. Location in patent: Page/Page column 16; 18
[3] Patent: WO2015/39348, 2015, A1. Location in patent: Page/Page column 24; 25

3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD

Product: 3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid 119736-16-2
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1000kg
Release date: 2025-09-19

Moxin Chemicals

Product: Baloxavir Impurity 31
Price: US $0.00-0.00/mg
Min. Order: 10mg
Purity: 99%+ HPLC
Supply Ability: 1000
Release date: 2025-06-04

Wuhan Biocar Pharmacy CO.,Ltd.

Product: 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid 119736-16-2
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 600kg
Release date: 2025-02-25

119736-16-2, 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acidRelated Search:

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

4-oxo-3-((phenylmethyl)oxy)-4h-pyran-2-carboxylic acid

4-Oxo-3-(phenylmethoxy)-4H-pyran-2-carboxylic acid

4-oxo-3-phenylmethoxypyran-2-carboxylic acid

4H-Pyran-2-carboxylic acid, 4-oxo-3-(phenylmethoxy)-

Baloxavir Impurity 31

Baloxavir Marboxil Impurity 2

Pinacol 1 - (1-ethoxyethyl) - 4-pyrazole borate

BPCA

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

3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid,119736-16-2

3-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid, 95+%

4-Oxo-3-(benzyloxy)-4H-pyran-2-carboxylic acid

3-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid, >97%

Baloxavixate Impurity 4

119736-16-2