N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine

Base Information

• Chemical Name: N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine
• CAS No.: 865362-42-1
• Molecular Formula: C₄₄H₅₄F₃N₅O₁₀SSi
• Molecular Weight: 930.087
• Mol file: 865362-42-1.mol

Synonyms:N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine

Chemical Property of N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine

There total 2 articles about N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine 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:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (865362-40-9) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine (865362-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / iPr₂NEt; CF₃COOK; 18-crown-6-ether / toluene / 11 h / 80 °C

2: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

With dmap; 18-crown-6 ether; potassium trifluoroacetate; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/ja051694k

Reference yield:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine (415707-13-0) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine (865362-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

2: 89 percent / iPr₂NEt; CF₃COOK; 18-crown-6-ether / toluene / 11 h / 80 °C

3: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

With dmap; 18-crown-6 ether; potassium trifluoroacetate; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/ja051694k

Reference yield:

N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine (865362-42-1) → N6-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylselenoadenosine 3'-(2-cyanoethyl)-N,N-diisopropylphosphoramidite

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaBH₄ / tetrahydrofuran; ethanol / 1 h / 20 °C

1.2: 49 percent / tetrahydrofuran / 0.33 h / 20 °C

2.1: 84 percent / TBAF; AcOH / tetrahydrofuran / 2.5 h / 20 °C

3.1: Me₂NEt / CH₂Cl₂ / 0.25 h / 20 °C

3.2: 91 percent / CH₂Cl₂ / 2 h / 20 °C

With sodium tetrahydroborate; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja051694k

upstream raw materials:

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine

Downstream raw materials:

N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-methylselenoadenosine