N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide

Base Information

• Chemical Name: N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide
• CAS No.: 1338921-55-3
• Molecular Formula: C₃₈H₃₆FN₃O₈
• Molecular Weight: 681.718

Synonyms:N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide

Chemical Property of N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide

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Technology Process of N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide

There total 2 articles about N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide 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: 80.0%

carbon monoxide (201230-82-2) + 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-iodouridine (104375-88-4) + para-fluorobenzylamine (140-75-0) → N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide (1338921-55-3)

Guidance literature:

With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 24h; under 2068.65 Torr; chemoselective reaction; Inert atmosphere; Autoclave;

DOI:10.1055/s-0039-1690190

Reference yield: 64.0%

para-fluorobenzylamine (140-75-0) + 5'-O-DMT-5-(2,2,2-trifluoroethyloxy-carbonyl)-2'-deoxyuridine (186553-11-7) → N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide (1338921-55-3)

Guidance literature:

With triethylamine; In acetonitrile; at 60 - 70 ℃; Inert atmosphere;

Reference yield: 80.0%

N-(4-fluorobenzyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyuridine-5-carboxamide (1338921-55-3) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-(4,4'-dimethoxytrityl)-5-(4-fluorobenzylaminocarbonyl)-3'-O-[(2-cyanoethyl)(N,N-diisopropylamino)phosphinyl]-2'-deoxyuridine (1338921-60-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 ℃; for 1h; Inert atmosphere;

upstream raw materials:

para-fluorobenzylamine

5'-O-DMT-5-(2,2,2-trifluoroethyloxy-carbonyl)-2'-deoxyuridine

carbon monoxide

2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-iodouridine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-5-(4-fluorobenzylaminocarbonyl)-3'-O-[(2-cyanoethyl)(N,N-diisopropylamino)phosphinyl]-2'-deoxyuridine

5-(4-fluorobenzylaminocarbonyl)-3'-O-acetyl-2'-deoxyuridine

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