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

Base Information

• Chemical Name: O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]-N²-phenoxyacetylguanosine
• CAS No.: 767338-09-0
• Molecular Formula: C₅₁H₆₀Cl₃N₅O₁₀Si
• Molecular Weight: 1037.51
• Mol file: 767338-09-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about O⁶-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]-N²-phenoxyacetylguanosine 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: 97.0%

N2,3'-O-bis(phenoxyacetyl)-O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-08-9) → O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]-N2-phenoxyacetylguanosine (767338-09-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 0.05h;

DOI:10.1002/anie.200460068

Reference yield:

Phenoxyacetyl chloride (701-99-5) → O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]-N2-phenoxyacetylguanosine (767338-09-0)

Guidance literature:

Multi-step reaction with 4 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

4: 97 percent / aq. NaOH / tetrahydrofuran; methanol / 0.05 h / 0 °C

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

DOI:10.1002/anie.200460068

Reference yield:

5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (312709-92-5) → O6-(2,2,2-trichloroethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]-N2-phenoxyacetylguanosine (767338-09-0)

Guidance literature:

Multi-step reaction with 4 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

4: 97 percent / aq. NaOH / tetrahydrofuran; methanol / 0.05 h / 0 °C

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

DOI:10.1002/anie.200460068

upstream raw materials:

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

Phenoxyacetyl chloride

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

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