N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide

Base Information

• Chemical Name: N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide
• CAS No.: 503157-93-5
• Molecular Formula: C₂₆H₃₈N₂O₉
• Molecular Weight: 522.596
• Mol file: 503157-93-5.mol

Synonyms:N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide

Chemical Property of N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide

There total 4 articles about N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide 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: 79.0%

N-α-(acetyl-tert-butoxycarbonyl)-O-(tert-butyl(dimethyl)silyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide (503157-92-4) → N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide (503157-93-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jm021016y

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide (503157-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / (iPr)2NEt; DMAP / CH₂Cl₂ / 20 °C

2: 79 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With dmap; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm021016y

Reference yield:

N-acetyl-L-tryrosinamide (1948-71-6) → N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide (503157-93-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / imidazole; pyridine / 4 h

2: 52 percent / (iPr)2NEt; DMAP / CH₂Cl₂ / 20 °C

3: 79 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm021016y

upstream raw materials:

N-α-(acetyl-tert-butoxycarbonyl)-O-(tert-butyl(dimethyl)silyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide

di-tert-butyl dicarbonate

N-acetyl-L-tryrosinamide

N-α-acetyl-O-(tert-butyl(dimethyl)silyl)-L-tyrosinamide

Downstream raw materials:

O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite

O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate