N²,3'-O-bis(phenoxyacetyl)-O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine

Base Information

• Chemical Name: N²,3'-O-bis(phenoxyacetyl)-O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine
• CAS No.: 767338-08-9
• Molecular Formula: C₅₉H₆₆Cl₃N₅O₁₂Si
• Molecular Weight: 1171.64

Synonyms:N²,3'-O-bis(phenoxyacetyl)-O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine

Chemical Property of N²,3'-O-bis(phenoxyacetyl)-O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of N²,3'-O-bis(phenoxyacetyl)-O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine

There total 4 articles about N²,3'-O-bis(phenoxyacetyl)-O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]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:

1,1,1-trichloroethanol (115-20-8) + Phenoxy-acetic acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[2-(2-phenoxy-acetylamino)-6-(2,4,6-trimethyl-benzenesulfonyloxy)-purin-9-yl]-4-triisopropylsilanyloxymethoxy-tetrahydro-furan-3-yl ester (767338-07-8) → N2,3'-O-bis(phenoxyacetyl)-O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-08-9)

Guidance literature:

With N,N-dimethyl-ethanamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/anie.200460068

Reference yield:

Phenoxyacetyl chloride (701-99-5) → N2,3'-O-bis(phenoxyacetyl)-O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Pyridine / CH₂Cl₂ / 2 h / 0 °C

2: DMAP; Et₃N / CH₂Cl₂ / 1 h / 20 °C

3: 129 mg / EtNMe₂; DBU / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; N,N-dimethyl-ethanamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane;

DOI:10.1002/anie.200460068

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (312709-92-5) → N2,3'-O-bis(phenoxyacetyl)-O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Pyridine / CH₂Cl₂ / 2 h / 0 °C

2: DMAP; Et₃N / CH₂Cl₂ / 1 h / 20 °C

3: 129 mg / EtNMe₂; DBU / CH₂Cl₂ / 2 h / 20 °C

With pyridine; dmap; N,N-dimethyl-ethanamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane;

DOI:10.1002/anie.200460068

upstream raw materials:

1,1,1-trichloroethanol

Phenoxy-acetic acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[2-(2-phenoxy-acetylamino)-6-(2,4,6-trimethyl-benzenesulfonyloxy)-purin-9-yl]-4-triisopropylsilanyloxymethoxy-tetrahydro-furan-3-yl ester

Phenoxyacetyl chloride

5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine

Downstream raw materials:

O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]-N²-phenoxyacetylguanosine

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