diMethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-

Base Information

• Chemical Name: diMethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-
• CAS No.: 1246616-66-9
• Molecular Formula: C16H14O7
• Molecular Weight: 318.283
• Mol file: 1246616-66-9.mol

Synonyms:diMethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-;4-Oxo-3-(phenylMethoxy)-4H-pyran-2,5-dicarboxylic acid 2,5-diMethyl ester;Dimethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate;Dolutegravir Intermediate3;Dolutegravir DL4B

Chemical Property of diMethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-

Chemical Property:

• Boiling Point: 534.9±50.0 °C(Predicted)
• PSA: 92.04000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 1.79200
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dimethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate is a useful intermediate for the preparation of dolutegravir and dolutegravir salts used in antiretroviral medications.

Technology Process of diMethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-

There total 4 articles about diMethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5- 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: 90.0%

Dimethyl oxalate (553-90-2) + methyl 4-benzyloxy-2-((dimethylamino)methylene)acetoacetate (1246616-65-8) → dimethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate (1246616-66-9)

Guidance literature:

With sodium t-butanolate; In toluene; at 105 ℃; for 6h;

Reference yield:

Methyl 4-chloroacetoacetate (32807-28-6,935731-94-5) → dimethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate (1246616-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tert-pentoxide / tetrahydrofuran / 2 h / 20 - 40 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Cooling with ice

2.1: 1,4-dioxane / 6 h / 20 °C

3.1: sodium t-butanolate / 1,3-dimethyl-2-imidazolidinone / 7 h / 20 - 30 °C / Inert atmosphere

3.2: 15 h / 20 °C

With sodium tert-pentoxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1,3-dimethyl-2-imidazolidinone;

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → dimethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate (1246616-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tert-pentoxide / tetrahydrofuran / 2 h / 20 - 40 °C / Inert atmosphere

1.2: 2 h / 0 - 20 °C / Cooling with ice

2.1: 1,4-dioxane / 6 h / 20 °C

3.1: sodium t-butanolate / 1,3-dimethyl-2-imidazolidinone / 7 h / 20 - 30 °C / Inert atmosphere

3.2: 15 h / 20 °C

With sodium tert-pentoxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1,3-dimethyl-2-imidazolidinone;

upstream raw materials:

Methyl 4-chloroacetoacetate

benzyl alcohol

4-benzyloxy-3-oxobutyric acid methyl ester

Dimethyl oxalate

Downstream raw materials:

C₂₁H₂₄N₂O₈

C₃₀H₃₄N₂O₈

dimethyl (S)-3-(benzyloxy)-1-(3-((tert-butoxycarbonyl)amino)-1,1-diphenylpropan-2-yl)-4-oxo-1,4-dihydropyridine-2,5-dicarboxylate

C₃₆H₃₈N₂O₈

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、 -. "PROCESS FOR PREPARING COMPOUND HAVING HIV INTEGRASE INHIBITORY ACTIVITY". . . Retrieved 2013/06/27.