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

Base Information

• Chemical Name: O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite
• CAS No.: 503157-97-9
• Molecular Formula: C₃₉H₆₄N₃O₁₁PS
• Molecular Weight: 813.99
• Mol file: 503157-97-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite 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: 65.0%

t-BuSATE phosphorodiamidite + N-α-(acetyl-tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide (503157-93-5) → O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite (503157-97-9)

Guidance literature:

With 1H-tetrazole; 3 A molecular sieve; diisopropylamine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/jm021016y

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite (503157-97-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 65 percent / 3 Angstroem molecular sieves; 1H-tetrazole; NH(iPr)2 / acetonitrile / 2 h / 20 °C

With 1H-tetrazole; dmap; 3 A molecular sieve; tetrabutyl ammonium fluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm021016y

Reference yield:

N-acetyl-L-tryrosinamide (1948-71-6) → O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite (503157-97-9)

Guidance literature:

Multi-step reaction with 4 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

4: 65 percent / 3 Angstroem molecular sieves; 1H-tetrazole; NH(iPr)2 / acetonitrile / 2 h / 20 °C

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; 3 A molecular sieve; tetrabutyl ammonium fluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm021016y

upstream raw materials:

N-α-(acetyl-tert-butoxycarbonyl)-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)-3'-azido-3'-deoxythymidin-5'-yl phosphate