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

Base Information

Chemical Name:O-[N-Boc-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate
CAS No.:503157-87-7
Molecular Formula:C₄₁H₆₀N₇O₁₅PS
Molecular Weight:954.005
Hs Code.:

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

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

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

There total 8 articles about O-[N-Boc-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate 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:

: C₄₁H₆₀N₇O₁₄PS

: 503157-87-7
O-[N-Boc-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Guidance literature:: With tert.-butylhydroperoxide; In toluene; acetonitrile; for 1h;
DOI:10.1021/jm021016y

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 503157-87-7
O-[N-Boc-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / (iPr)2NEt; DMAP / CH₂Cl₂

2: 91 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

3: 60 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:

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 503157-87-7
O-[N-Boc-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-3'-azido-3'-deoxythymidin-5'-yl phosphate

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / NH₃ / methanol / 60 h / 5 °C

2: 70 percent / imidazole; pyridine / 4 h

3: 85 percent / (iPr)2NEt; DMAP / CH₂Cl₂

4: 91 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

5: 60 percent / 3 Angstroem molecular sieves; 1H-tetrazole; NH(iPr)2 / acetonitrile / 2 h / 20 °C

6: 3 Angstroem molecular sieves; 1H-tetrazole / acetonitrile / 1 h

7: tBuOOH / toluene; acetonitrile / 1 h

With pyridine; 1H-imidazole; 1H-tetrazole; tert.-butylhydroperoxide; dmap; 3 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm021016y