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

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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

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.

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.

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).

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

Raw materials

Preparation Products

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

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

ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Baloxavir Marboxil Impurity 4 119736-16-2
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
0.98
Supply Ability
10g
Release date
2024-04-28
ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Baloxavir Marboxil Impurity 4 119736-16-2
Price
US $0.00/mg
Min. Order
10mg
Purity
0.98
Supply Ability
10g
Release date
2024-04-01
PNP Biotech Co. Ltd
Product
3-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid 119736-16-2
Price
US $0.00/kg
Min. Order
25kg
Purity
98%
Supply Ability
Inquiry
Release date
2022-10-20

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
  • 119736-16-2
  • 119736-16-2