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

Base Information

• Chemical Name: N²,3'-O-bis(phenoxyacetyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine
• CAS No.: 767338-06-7
• Molecular Formula: C₅₇H₆₅N₅O₁₂Si
• Molecular Weight: 1040.25
• Mol file: 767338-06-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about N²,3'-O-bis(phenoxyacetyl)-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: 74.0%

Phenoxyacetyl chloride (701-99-5) + 5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(triisopropylsilyl)oxy]methyl}guanosine (312709-92-5) → N2,3'-O-bis(phenoxyacetyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-06-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/anie.200460068

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) + N2,3'-O-bis(phenoxyacetyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-06-7) → 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)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/anie.200460068

Reference yield:

N2,3'-O-bis(phenoxyacetyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-[[(triisopropyl)silyloxy]methyl]guanosine (767338-06-7) → 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 3 steps

1: DMAP; Et₃N / CH₂Cl₂ / 1 h / 20 °C

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

3: 97 percent / aq. NaOH / tetrahydrofuran; methanol / 0.05 h / 0 °C

With 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:

Phenoxyacetyl chloride

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

Downstream raw materials:

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

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

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