5'-Thymidylic acid, 3'-azido-3'-deoxy-, 4-[(2S)-2-[acetyl[(1,1-dimethylethoxy)carbonyl]amino]-3-[bis[(1,1-dimeth ylethoxy)carbonyl]amino]-3-oxopropyl]phenyl 2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl ester

Base Information

• Chemical Name: 5'-Thymidylic acid, 3'-azido-3'-deoxy-, 4-[(2S)-2-[acetyl[(1,1-dimethylethoxy)carbonyl]amino]-3-[bis[(1,1-dimeth ylethoxy)carbonyl]amino]-3-oxopropyl]phenyl 2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl ester
• CAS No.: 503157-88-8
• Molecular Formula: C43H62N7O16PS
• Molecular Weight: 996.042
• Mol file: 503157-88-8.mol

Synonyms:

Chemical Property of 5'-Thymidylic acid, 3'-azido-3'-deoxy-, 4-[(2S)-2-[acetyl[(1,1-dimethylethoxy)carbonyl]amino]-3-[bis[(1,1-dimeth ylethoxy)carbonyl]amino]-3-oxopropyl]phenyl 2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-Thymidylic acid, 3'-azido-3'-deoxy-, 4-[(2S)-2-[acetyl[(1,1-dimethylethoxy)carbonyl]amino]-3-[bis[(1,1-dimeth ylethoxy)carbonyl]amino]-3-oxopropyl]phenyl 2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl ester

There total 8 articles about 5'-Thymidylic acid, 3'-azido-3'-deoxy-, 4-[(2S)-2-[acetyl[(1,1-dimethylethoxy)carbonyl]amino]-3-[bis[(1,1-dimeth ylethoxy)carbonyl]amino]-3-oxopropyl]phenyl 2-[(2,2-dimethyl-1-oxopropyl)thio]ethyl 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:

C43H62N7O15PS → O-[N-(acetyl-Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate (503157-88-8)

Guidance literature:

With tert.-butylhydroperoxide; In toluene; acetonitrile; for 1h;

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)-3'-azido-3'-deoxythymidin-5'-yl phosphate (503157-88-8)

Guidance literature:

Multi-step reaction with 5 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

4: 3 Angstroem molecular sieves; 1H-tetrazole / acetonitrile / 1 h

5: tBuOOH / toluene; acetonitrile / 1 h

With 1H-tetrazole; tert.-butylhydroperoxide; dmap; 3 A molecular sieve; tetrabutyl ammonium fluoride; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 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)-3'-azido-3'-deoxythymidin-5'-yl phosphate (503157-88-8)

Guidance literature:

Multi-step reaction with 6 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

5: 3 Angstroem molecular sieves; 1H-tetrazole / acetonitrile / 1 h

6: tBuOOH / toluene; acetonitrile / 1 h

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

DOI:10.1021/jm021016y

upstream raw materials:

di-tert-butyl dicarbonate

N-acetyl-L-tryrosinamide

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

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