2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one

Base Information

• Chemical Name: 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one
• CAS No.: 1206102-04-6
• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.361
• Mol file: 1206102-04-6.mol

Synonyms:2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one

Chemical Property of 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3-Benzyloxy-2-(2-hydroxy-2-phenylethyl)-4H-pyran-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-Benzyloxy-2-(2-hydroxy-2-phenylethyl)-4H-pyran-4-one is an intermediate in the synthesis of Dolutegravir (D528800), a second generation HIV-1 integrase strand transfer inhibitor.

Technology Process of 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one

There total 4 articles about 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one 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: 83.0%

Maltol (118-71-8) + benzyl bromide (100-39-0) + benzaldehyde (100-52-7) → 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one (1206102-04-6)

Guidance literature:

Maltol; benzyl bromide;

With lithium hexamethyldisilazane;

benzaldehyde; at -65 ℃;

DOI:10.1021/acs.oprd.8b00410

Reference yield:

3-O-benzylmaltol (61049-69-2) + benzaldehyde (100-52-7) → 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one (1206102-04-6)

Guidance literature:

3-O-benzylmaltol; benzaldehyde; With lithium hexamethyldisilazane; In tetrahydrofuran; at -60 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; water; ethyl acetate;

Reference yield:

Maltol (118-71-8) → 2-(2-hydroxy-2-phenylethyl)-3-[(phenylmethyl)oxy]-4H-pyran-4-one (1206102-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / acetonitrile / Inert atmosphere; Reflux; Large scale

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -60 °C / Inert atmosphere

2.2: 2 h / -60 °C / Inert atmosphere

With potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;

upstream raw materials:

3-O-benzylmaltol

benzaldehyde

Maltol

benzyl bromide

Downstream raw materials:

2-[(E)-2-phenylethenyl]-3-[(phenylmethyl)oxy]-4H-pyran-4-one

{[(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

methyl 3-(benzyloxy)-5-(2,4-difluorobenzylcarbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate

5-({[(2,4-difluorophenyl)methyl]amino}carbonyl)-1-[2-hydroxy-2-(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid methyl ester

Refernces

• 1、 Yasukata, Tatsuro,Masui, Moriyasu,Ikarashi, Fumiya,Okamoto, Kazuya,Kurita, Takanori,Nagai, Masahiko,Sugata, Yoshihide,Miyake, Naoki,Hara, Shinichiro,Adachi, You,Sumino, Yukihito. "Practical Synthetic Method for the Preparation of Pyrone Diesters: An Efficient Synthetic Route for the Synthesis of Dolutegravir Sodium". . p. 565 - 570. Retrieved 2019/03/26.
• 2、 -. "Intermediate of these pyridonecarboxylic carbamoylalkanoic and HIV integrase inhibitor". Paragraph 0030; 0036. . Retrieved 2016/10/07.