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

Base Information

• Chemical Name: N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine
• CAS No.: 865362-40-9
• Molecular Formula: C₄₄H₅₄F₃N₅O₁₀SSi
• Molecular Weight: 930.087
• Mol file: 865362-40-9.mol

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

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

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}adenosine

There total 1 articles about N⁶-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-trifluoromethanesulfonyl-3'-O-{[(triisopropylsilyl)oxy]methyl}adenosine 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: 60.0%

trifluoromethane sulfonyl chloride (421-83-0) + 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}adenosine (865362-40-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/ja051694k

Reference yield: 89.0%

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)-3'-O-{[(triisopropylsilyl)oxy]methyl}(β-D-arabinofuranosyl)adenine (865362-41-0)

Guidance literature:

With 18-crown-6 ether; potassium trifluoroacetate; N-ethyl-N,N-diisopropylamine; In toluene; at 80 ℃; for 11h;

DOI:10.1021/ja051694k

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'-deoxy-2'-methylselenoadenosine (865362-44-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / iPr₂NEt; CF₃COOK; 18-crown-6-ether / toluene / 11 h / 80 °C

2.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.33 h / 20 °C

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

3.2: 49 percent / tetrahydrofuran / 0.33 h / 20 °C

4.1: 84 percent / TBAF; AcOH / tetrahydrofuran / 2.5 h / 20 °C

With dmap; sodium tetrahydroborate; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium trifluoroacetate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/ja051694k

upstream raw materials:

trifluoromethane sulfonyl chloride

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

Downstream raw materials:

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

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

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

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