6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

Base Information

• Chemical Name: 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)
• CAS No.: 1082489-87-9
• Molecular Formula: C₄₂H₅₁N₈O₅PS
• Molecular Weight: 810.957
• Mol file: 1082489-87-9.mol

Synonyms:

Chemical Property of 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)

There total 7 articles about 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-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: 70.0%

6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine (1233510-66-1) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (1082489-87-9)

Guidance literature:

With 1H-tetrazole; diisopropylamine; In dichloromethane; for 8h;

DOI:10.1039/b9nj00678h

Reference yield:

5'-O-(4,4'-Dimethoxytrityl)-N6-dimethylformamidine-2'-deoxyadenosine (17331-20-3,869355-14-6) → 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (1082489-87-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

2.1: trifluoroacetic acid / dichloromethane / 0.02 h

3.1: methanol / 3 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C

4.2: 1 h / 20 °C

5.1: triethylamine tris(hydrogen fluoride); triethylamine / tetrahydrofuran / 24 h

6.1: 1H-tetrazole; diisopropylamine / dichloromethane / 8 h

With 1H-imidazole; 1H-tetrazole; n-butyllithium; triethylamine tris(hydrogen fluoride); triethylamine; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b9nj00678h

Reference yield:

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-6-N-[(dimethylamino)methylene]-2'-deoxyadenosine (1233510-51-4) → 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) (1082489-87-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trifluoroacetic acid / dichloromethane / 0.02 h

2.1: methanol / 3 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C

3.2: 1 h / 20 °C

4.1: triethylamine tris(hydrogen fluoride); triethylamine / tetrahydrofuran / 24 h

5.1: 1H-tetrazole; diisopropylamine / dichloromethane / 8 h

With 1H-tetrazole; n-butyllithium; triethylamine tris(hydrogen fluoride); triethylamine; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b9nj00678h

upstream raw materials:

6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine

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

3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-6-N-[(dimethylamino)methylene]-2'-deoxyadenosine

3'-O-(tert-butyldimethylsilyl)-6-N-[(dimethylamino)methylene]-2'-deoxyadenosine