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

Base Information

Chemical Name:O-[N-(Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite
CAS No.:503157-98-0
Molecular Formula:C₃₇H₆₂N₃O₁₀PS
Molecular Weight:771.953
Hs Code.:

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

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

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

There total 6 articles about O-[N-(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: 60.0%

: t-BuSATE phosphorodiamidite

: 503157-95-7
N-α-(tert-butoxycarbonyl)-N,N-di(tert-butoxycarbonyl)-L-tyrosinamide

: 503157-98-0
O-[N-(Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite

Guidance literature:: With 1H-tetrazole; 3 A molecular sieve; diisopropylamine; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1021/jm021016y

Reference yield:

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

: 503157-98-0
O-[N-(Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite

Guidance literature:: Multi-step reaction with 3 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

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:

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

: 503157-98-0
O-[N-(Boc)-L-tyrosinyl-N,N-di-Boc-amide]-O-(S-pivaloyl-2-thioethyl)-N,N-diisopropyl phosphoramidite

Guidance literature:: Multi-step reaction with 5 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

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