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
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
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.
N-Bromosuccinimide Price
- Product number
- O858450
- Product name
- 4-Oxo-3-[(phenylmethyl)oxy]-4H-pyran-2-carboxylicAcid
- Packaging
- 250mg
- Price
- $580
- Updated
- 2021/12/16
- Product number
- CS-0051716
- Product name
- 3-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylicacid
- Purity
- 99.97%
- Packaging
- 10g
- Price
- $77
- Updated
- 2021/12/16
- Product number
- 7515CZ
- Product name
- 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylicacid
- Packaging
- 5g
- Price
- $119
- Updated
- 2021/12/16
- Product number
- FB167699
- Product name
- 3-Benzyloxy-4-oxo-4H-pyran-2-carboxylic acid
- Packaging
- 5G
- Price
- $125
- Updated
- 2021/12/16
- Product number
- CS-0051716
- Product name
- 3-(Benzyloxy)-4-oxo-4H-pyran-2-carboxylicacid
- Purity
- 99.97%
- Packaging
- 25g
- Price
- $132
- Updated
- 2021/12/16
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
3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid Suppliers
- Tel
- +1-2266000236
- sales@rdscientific.com
- Country
- Canada
- ProdList
- 1914
- Advantage
- 58
View Lastest Price from 3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid manufacturers
- 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
- 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
- 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