3 -TRNH-DT-5 -CEPA

Base Information

• Chemical Name: 3 -TRNH-DT-5 -CEPA
• CAS No.: 195375-68-9
• Molecular Formula: C38H46 N5 O5 P
• Molecular Weight: 683.787
• Mol file: 195375-68-9.mol

Synonyms:Thymidine,3'-deoxy-3'-[(triphenylmethyl)amino]-, 5'-[2-cyanoethylbis(1-methylethyl)phosphoramidite] (9CI)

Chemical Property of 3 -TRNH-DT-5 -CEPA

Chemical Property:

• PKA: 9.55±0.10(Predicted)
• PSA: 135.20000
• LogP: 6.76628

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3 -TRNH-DT-5 -CEPA

There total 8 articles about 3 -TRNH-DT-5 -CEPA 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: 95.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 1-[(2R,4S,5S)-5-Hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (195375-41-8) → 3'-NH-trityl-3'-aminothymidine 5'-O-cyanoethyl-N,N-diisopropylaminophosphoramidite (195375-68-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.25h;

DOI:10.1021/jo970801t

Reference yield:

3'-amino-3'-deoxythymidine (52450-18-7) → 3'-NH-trityl-3'-aminothymidine 5'-O-cyanoethyl-N,N-diisopropylaminophosphoramidite (195375-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine; triethylamine

2: diisopropylammonium tetrazolide

With pyridine; N,N-diisopropylamine tetrazolide; triethylamine;

DOI:10.1081/NCN-200060068

Reference yield:

3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine (134077-32-0) → 3'-NH-trityl-3'-aminothymidine 5'-O-cyanoethyl-N,N-diisopropylaminophosphoramidite (195375-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / H₂ / 10percent Pd/C / ethanol

2: 90 percent / Et₃N / pyridine / 4 h / Ambient temperature

3: 90 percent / 2 M NaOH / dioxane; methanol / 1.5 h / Ambient temperature

4: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 0.25 h

With sodium hydroxide; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane;

DOI:10.1021/jo970801t

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

1-[(2R,4S,5S)-5-Hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

trityl chloride

Refernces

• 1、 Zielinska, Daria,Pongracz, Krisztina,Gryaznov, Sergei M.. "A new approach to oligonucleotide N3′ → P5′ phosphoramidate building blocks". . p. 4495 - 4499. Retrieved 2007/10/03.
• 2、 Nelson, Jeffrey S.,Fearon, Karen L.,Nguyen, Mark Q.,McCurdy, Sarah N.,Frediani, Jeff E.,Foy, Michael F.,Hirschbein, Bernard L.. "N3′→P5′ Oligodeoxyribonucleotide Phosphoramidates: A New Method of Synthesis Based on a Phosphoramidite Amine-Exchange Reaction". . p. 7278 - 7287. Retrieved 2007/10/03.