3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine

Base Information

• Chemical Name: 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine
• CAS No.: 1257514-30-9
• Molecular Formula: C₅₁H₅₉N₈O₉P
• Molecular Weight: 959.051

Synonyms:3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine

Chemical Property of 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine

Chemical Property:

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Technology Process of 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine

There total 6 articles about 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine 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%

5'-O-(4,4'-dimethoxytrityl)-N2-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine (1257514-44-5) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine (1257514-30-9)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1021/ja106158b

Reference yield:

(p-hydroxyphenyl)boronic acid (71597-85-8) → 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine (1257514-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tris-(2-sulfophenyl)phosphine trisodium salt; palladium diacetate; sodium carbonate / water; acetonitrile / 4 h / 80 °C / Inert atmosphere

2.1: methanol / 96 h / 20 °C

3.1: pyridine; triethylamine / 2.5 h / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 20 °C

4.2: 0.5 h / 20 °C

5.1: triethylamine / acetonitrile / 0.5 h / 20 °C

With pyridine; tris-(2-sulfophenyl)phosphine trisodium salt; potassium tert-butylate; palladium diacetate; sodium carbonate; triethylamine; In tetrahydrofuran; methanol; water; acetonitrile; 1.1: Suzuki-Miyaura coupling;

DOI:10.1021/ja106158b

Reference yield:

8-(4''-hydroxyphenyl)-2'-deoxyguanosine (143084-40-6) → 3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-N2-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine (1257514-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanol / 96 h / 20 °C

2.1: pyridine; triethylamine / 2.5 h / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 20 °C

3.2: 0.5 h / 20 °C

4.1: triethylamine / acetonitrile / 0.5 h / 20 °C

With pyridine; potassium tert-butylate; triethylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ja106158b

upstream raw materials:

8-(4''-hydroxyphenyl)-2'-deoxyguanosine

N₂-(N,N-dimethylformamidinyl)-8-(4''-hydroxyphenyl)-2'-deoxyguanosine

5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-hydroxyphenyl)-2'-deoxyguanosine

5'-O-(4,4'-dimethoxytrityl)-N₂-(N,N-dimethylformamidinyl)-8-(4''-acetoxyphenyl)-2'-deoxyguanosine

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