O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite

Base Information

• Chemical Name: O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite
• CAS No.: 312750-65-5
• Molecular Formula: C₂₈H₄₇N₂O₇PS
• Molecular Weight: 586.73

Synonyms:O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite

Chemical Property of O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite

There total 1 articles about O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite 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: 87.0%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) + S-pivaloyl-2-thioethyl di(N,N-diisopropylamino)phosphoramidite (200502-01-8) → O-(Nα-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite (312750-65-5)

Guidance literature:

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

DOI:10.1021/jm000996o

Reference yield:

O-(Nα-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite (312750-65-5) → O-(Nα-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate (312750-69-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: t-BuOOH / acetonitrile; toluene / 1 h

With 1H-tetrazole; tert.-butylhydroperoxide; 3 A molecular sieve; In toluene; acetonitrile;

DOI:10.1021/jm000996o

Reference yield:

O-(Nα-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite (312750-65-5) → O-(L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate

Guidance literature:

Multi-step reaction with 3 steps

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

2: t-BuOOH / acetonitrile; toluene / 1 h

3: TFA / CH₂Cl₂

With 1H-tetrazole; tert.-butylhydroperoxide; 3 A molecular sieve; trifluoroacetic acid; In dichloromethane; toluene; acetonitrile;

DOI:10.1021/jm000996o

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

S-pivaloyl-2-thioethyl di(N,N-diisopropylamino)phosphoramidite

Downstream raw materials:

(S)-3-(4-{[(2S,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphanyloxy}-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

O-(N^α-tert-butoxycarbonyl-L-methoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate

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