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

Base Information

• Chemical Name: O-(N^α-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate
• CAS No.: 312750-67-7
• Molecular Formula: C₃₅H₅₁N₆O₁₂PS
• Molecular Weight: 810.863

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about O-(N^α-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',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:

(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 tert-butyl ester (855429-61-7) → O-(Nα-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate (312750-67-7)

Guidance literature:

With tert.-butylhydroperoxide;

DOI:10.1016/S0960-894X(98)00535-6

Reference yield:

S-pivaloyl-2-thioethyl di(N,N-diisopropylamino)phosphoramidite (200502-01-8) → O-(Nα-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate (312750-67-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-tetrazole; HN(i-Pr)2 / acetonitrile

2: 1H-tetrazole / acetonitrile

3: t-BuOOH / toluene

With 1H-tetrazole; tert.-butylhydroperoxide; diisopropylamine; In toluene; acetonitrile;

DOI:10.1081/NCN-100002302

Reference yield:

O-(Nα-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) N,N-diisopropylphosphoramidite (312750-63-3) → O-(Nα-tert-butoxycarbonyl-L-tert-butoxytyrosinyl) O-(S-pivaloyl-2-thioethyl) 3'-azido-2',3'-deoxythymidin-5'-yl phosphate (312750-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-tetrazole / acetonitrile

2: t-BuOOH / toluene

With 1H-tetrazole; tert.-butylhydroperoxide; In toluene; acetonitrile;

DOI:10.1081/NCN-100002302

upstream 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 tert-butyl ester

Boc-Tyr-OH

(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

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

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