1206102-05-7

Basic information

• Product Name: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one
• Synonyms: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one
• CAS NO: 1206102-05-7
• Molecular Weight: 304.345
• Mol File: 1206102-05-7.mol

Chemical Properties

• CAS DataBase Reference: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one(1206102-05-7)
• EPA Substance Registry System: 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one(1206102-05-7)

Safety Data

• Hazardous Substances Data: 1206102-05-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one is used as an intermediate in the synthesis of Dolutegravir (D528800), a second-generation HIV-1 integrase strand transfer inhibitor. This application is significant because Dolutegravir is an essential drug in the treatment of HIV-1 infection, helping to suppress the viral load and prevent the progression of the disease.
In the synthesis process, 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one contributes to the formation of the final drug molecule, which targets the integrase enzyme responsible for integrating the viral DNA into the host cell's genome. By inhibiting this enzyme, Dolutegravir effectively disrupts the replication process of the HIV-1 virus, thus providing a valuable treatment option for patients living with HIV-1.
The use of 2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one in the pharmaceutical industry highlights its importance in the development of life-saving medications. Its role in the synthesis of Dolutegravir demonstrates the potential of this compound in addressing significant health challenges and improving the quality of life for individuals affected by HIV-1.

Upstream product

• 61049-69-2 3-O-benzylmaltol 
• 100-39-0 benzyl bromide 
• 118-71-8 Maltol 
• 1206102-04-6 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one 

Downstream Products

• 500371-01-7 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde 
• 119736-16-2 3-(benzyloxy)-1-((tert-butoxycarbonyl)amino)-4-oxo-1,4-dihydropyridine-2-carboxylic acid ethyl ester 
• 1051375-16-6 dolutegravir 
• 1051375-19-9 (4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1′,2′:4,5]pyrazino-[2,1-b][1,3]oxazine-9-carboxamide sodium salt 
• 1206102-09-1 (4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1′,2’:4,5] pyrazino[2,1-b][1,3]oxazine-6,8-dione 
• 1206784-52-2 {[(4aS,13aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-9,11-dioxo-2,3,4a,5,9,11,13,13a-octahydro-1H-pyrido[1,2-a]pyrrolo[1',2':3,4]imidazo[1,2-d]pyrazin-10-yl]oxy}methyl methyl carbonate 
• 1206103-64-1 (4aS,13aR)-8-bromo-10-[(phenylmethyl)oxy]-2,3,4a,5,13,13a-hexahydro-1H-pyrido[1,2-a]pyrrolo[1′,2′:3,4]imidazo[1,2-d]pyrazine-9,11-dione 
• 1206103-62-9 5-bromo-1-(2,3-dihydroxypropyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester 
• 1206103-65-2 (4aS,13aR)-N-[(2,4-difluorophenyl)methyl]-9,11-dioxo-10-[(phenylmethyl)oxy]-2,3,4a,5,9,11,13,13a-octahydro-1H-pyrido[1,2-a]pyrrolo[1′,2′,3, 4]imidazo[1,2-d]pyrazine-8-carboxamide 
• 1206168-05-9 {[(3S,11aR)-8-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazin-6-yl]oxy}methyl methyl carbonate 
• 1206103-45-8 (3S,11aR)-N-[(2,4-difluorophenyl)methyl]-3-methyl-5,7-dioxo-6-[(phenylmethyl)oxy]-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide 
• 1051375-10-0 (3S,11aR)-N-[(2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide 
• 1206103-44-7 (3S,11 aR)-8-bromo-3-methyl-6-[(phenyl-methyl)oxy]-2,3,11,11a-tetrahydro[1,3]oxazolo[3,2-a] pyrido[1,2-d]pyrazine-5,7-dione 
• 1206103-43-6 (3S,11aR)-3-methyl-6-[(phenylmethyl)oxy]-2,3,11,11a-tetrahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione 

Relevant articles and documents

Practical and Scalable Synthetic Method for Preparation of Dolutegravir Sodium: Improvement of a Synthetic Route for Large-Scale Synthesis

A practical and scalable synthetic method to obtain dolutegravir sodium (1) was established starting from the readily accessible material maltol (2). This synthetic method includes a scalable oxidation process of maltol and palladium-catalyzed amidation for introduction of an amide moiety, leading to a practical manufacturing method in short synthetic steps. The synthetic method demonstrated herein enables multikilogram scale manufacturing of 1 of high purity.

TETRACYCLIC HETEROCYCLE COMPOUNDS USEFUL AS HIV INTEGRASE INHIBITORS

The present invention relates to Tetracyclic Heterocycle Compounds of Formula (I) and pharmaceutically acceptable salts or prodrug thereof, wherein n, X, Y, Z, R1, R2, and R3 are as defined herein. The present invention also relates to compositions comprising at least one Tetracyclic Heterocycle Compound, and methods of using the Tetracyclic Heterocycle Compounds for treating or preventing HIV infection in a subject.

(3S,11aR)-6-[(phenylmethyl)oxy]-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-9 and/or (3S,11aR)-6-[(phenymethyl)oxy]-8-bromo-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-10

The compounds are intermediates in the preparation of therapeutic agents useful in the treatment of viral infections, particularly HIV infection. The compounds are (3S,11aR)-6-[(phenylmethyl)oxy]-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-9 and/or (3S,11aR)-6-[(phenylmethyl)oxy]-8-bromo-3-methyl-2,3,11,11a-tetrahydrooxazolo[3,2-a]pyrido[1,2-d]pyrazine-5,7-dione of the formula P-10.

CHEMICAL COMPOUNDS

The present invention features compounds that are prodrugs of HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

MALTOL ETHER PROCESSES AND INTERMEDIATES

Novel processes and intermediates are provided according to the general reaction scheme: Formula I, II, III, IV (I), (II), (III), (IV) utilizing a ruthenium catalyst in an oxidative cleavage of the triene 4 whereby an aldehyde may be produced and optionally taken on to a carboxylic acid 5: Formula V (V)