(R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate

Base Information

• Chemical Name: (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate
• CAS No.: 862421-95-2
• Molecular Formula: C₁₅H₂₁NO₄Se
• Molecular Weight: 358.296
• Mol file: 862421-95-2.mol

Synonyms:(R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate

Chemical Property of (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate

There total 10 articles about (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate 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: 85.0%

diphenyl diselenide (1666-13-3) + (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester (126496-79-5) → (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate (862421-95-2)

Guidance literature:

diphenyl diselenide; With indium iodide; In dichloromethane; at 20 ℃;

(S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/jo060286b

Reference yield: 61.0%

diphenyl diselenide (1666-13-3) + methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate (175844-11-8,402726-50-5) → (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate (862421-95-2)

Guidance literature:

diphenyl diselenide; With 1-butyl-3-methylimidazolium Tetrafluoroborate; zinc; at 20 ℃; Inert atmosphere;

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo100454m

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate (862421-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 94.3 percent / aq. NaOH / dioxane / 4.5 h / 5 - 20 °C

2.1: 72.3 percent / K₂CO₃ / dimethylformamide / 20 h / 0 °C

3.1: pyridine

4.1: NaBr

5.1: LiBEt₃H / tetrahydrofuran / 0 °C

5.2: 45 percent / NEt₃ / tetrahydrofuran / 20 h / 0 °C

With pyridine; sodium hydroxide; lithium triethylborohydride; potassium carbonate; sodium bromide; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1039/b505299h

upstream raw materials:

diazomethane

(S)-2-tert-butoxycarbonylamino-3-phenylselanylpropionic acid

diphenyl diselenide

methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate

Downstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-phenylselanylpropionic acid

L-(Se)-phenylselenocysteine