5'-O-(N⁶-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate

Base Information

• Chemical Name: 5'-O-(N⁶-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate
• CAS No.: 141928-26-9
• Molecular Formula: C₅₆H₆₆N₈O₁₃P₂S
• Molecular Weight: 1153.2

Synonyms:

Chemical Property of 5'-O-(N⁶-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 5'-O-(N⁶-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate

There total 4 articles about 5'-O-(N⁶-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate 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:

N,N-diisopropylmethylphosphonamidic chloride (86030-43-5) + 5'-O-(N6-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate (141955-64-8,142035-09-4) → 5'-O-(N6-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate (141928-26-9,142033-79-2,142033-81-6,142033-82-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h; Yield given;

DOI:10.1021/ja00040a004

Reference yield:

N6-benzoyl-3'-(methoxyacetyl)-2'-deoxyadenosine (25152-96-9) → 5'-O-(N6-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate (141928-26-9,142033-79-2,142033-81-6,142033-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tetrazole, 2.) S, 2,6-lutidine / 1.) CH₃CN, RT, 1 h, 2.) CH₃CN, CS₂, 1 h

2: aq. NH₃

3: i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; 1H-tetrazole; ammonium hydroxide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja00040a004

Reference yield:

[5'-O-(4,4'-dimethoxytrityl)thymidine-3'-yl]-(N,N'-diisopropyl)methylphosphoramidite (84416-85-3) → 5'-O-(N6-benzoyl-3'-O-(diisopropylaminomethoxyphosphino)-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate (141928-26-9,142033-79-2,142033-81-6,142033-82-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) tetrazole, 2.) S, 2,6-lutidine / 1.) CH₃CN, RT, 1 h, 2.) CH₃CN, CS₂, 1 h

2: aq. NH₃

3: i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; 1H-tetrazole; ammonium hydroxide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja00040a004

upstream raw materials:

N,N-diisopropylmethylphosphonamidic chloride

5'-O-(N⁶-benzoyl-2'-deoxyadenosyl) 3'-O-<5'-O-(dimethoxytrityl)thymidine> O-methyl phosphorothioate

N⁶-benzoyl-3'-(methoxyacetyl)-2'-deoxyadenosine

[5'-O-(4,4'-dimethoxytrityl)thymidine-3'-yl]-(N,N'-diisopropyl)methylphosphoramidite

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