N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine
• CAS No.: 753456-30-3
• Molecular Formula: C₃₄H₄₇N₈O₇PS
• Molecular Weight: 742.836

Synonyms:N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine

Chemical Property of N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine

Chemical Property:

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Technology Process of N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine

There total 6 articles about N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine 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: 69.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + N6-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-2'-deoxyadenosine (753456-26-7) → N6-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine (753456-30-3)

Guidance literature:

With triethylamine; In acetonitrile; at 25 ℃; for 1h;

DOI:10.1021/ja048377i

Reference yield:

2,2,5,5-tetramethyl-3-pyrroline-3-carboxamide (19805-75-5) → N6-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine (753456-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 40 percent / Br; aq. NaOH / 1 h / 100 °C

2.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C

2.2: 78 percent / CH₂Cl₂ / 2 h / 25 °C

3.1: 62 percent / hydrazine hydrate; pyridine; acetic acid / 0.05 h / 25 °C

4.1: 69 percent / triethylamine / acetonitrile / 1 h / 25 °C

With pyridine; sodium hydroxide; thionyl chloride; bromine; hydrazine hydrate; acetic acid; triethylamine; In acetonitrile; 1.1: Hofmann rearrangement;

DOI:10.1021/ja048377i

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-3'-O-levulinoyl-2'-deoxyadenosine (93134-36-2) → N6-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-3'-O-[(N,N-diisopropylamino)(2-cyanoethyloxy)]phosphinyl-2'-deoxyadenosine (753456-30-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / 0.5 h / 25 °C

2.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C

2.2: 78 percent / CH₂Cl₂ / 2 h / 25 °C

3.1: 62 percent / hydrazine hydrate; pyridine; acetic acid / 0.05 h / 25 °C

4.1: 69 percent / triethylamine / acetonitrile / 1 h / 25 °C

With pyridine; thionyl chloride; hydrazine hydrate; acetic acid; triethylamine; In acetonitrile;

DOI:10.1021/ja048377i

upstream raw materials:

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

N⁶-benzoyl-5'-O-(2,2,5,5-tetramethylpyrrolidin-3-one-1-sulfinyl)-2'-deoxyadenosine

2,2,5,5-tetramethyl-3-pyrroline-3-carboxamide

N-benzoyl-3'-O-levulinoyl-2'-deoxy-β-D-adenosine

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