(2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester
• CAS No.: 339178-17-5
• Molecular Formula: C₂₀H₂₄N₂O₆Se
• Molecular Weight: 467.38

Synonyms:(2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Chemical Property of (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

There total 7 articles about (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester 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: 57.0%

Phenylselenyl chloride (5707-04-0) + (2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-10-8) → (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-17-5) + (2R,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Guidance literature:

(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; cyclohexane; at -78 - 20 ℃;

With tert.-butyl lithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane; at -78 ℃; for 1h;

Phenylselenyl chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 1h; Further stages.;

DOI:10.1021/jo001223a

Reference yield:

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid (127244-82-0) → (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 23.5 h / 0 - 20 °C

2.1: 97 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

3.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / -78 - 20 °C

3.2: tBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

3.3: 57 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

With dmap; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; cyclohexane;

DOI:10.1021/jo001223a

Reference yield:

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester (127218-27-3) → (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester (339178-17-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

2.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / -78 - 20 °C

2.2: tBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

2.3: 57 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

With tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; cyclohexane;

DOI:10.1021/jo001223a

upstream raw materials:

Phenylselenyl chloride

(2S,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid

(2S,3S,5R)-3-(tert-butyldiphenylsilanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carboxylic acid tert-butyl ester

Downstream raw materials:

1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-5-phenylselenenyltetrahydrofuran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 339178-17-5 (2S,4S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(phenylselenenyl)tetrahydrofuran-2-carboxylic acid tert-butyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send