2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Base Information

• Chemical Name: 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine
• CAS No.: 199793-01-6
• Molecular Formula: C₄₈H₄₅N₇O₁₂
• Molecular Weight: 911.925

Synonyms:2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Chemical Property of 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Chemical Property:

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Technology Process of 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

There total 6 articles about 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 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%

Carbonic acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester (199792-99-9) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199793-01-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.0166667h;

DOI:10.1080/07328319708006249

Reference yield: 95.0%

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199792-92-2) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199793-01-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 288h;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (199793-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine / CH₂Cl₂ / 32 h / 20 °C

2: 95 percent / DBU / acetonitrile / 0.02 h / 20 °C

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; 1: Condensation / 2: Elimination;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

upstream raw materials:

Carbonic acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

4,4'-dimethoxytrityl chloride

2'-deoxy-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Downstream raw materials:

2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)

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