2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine

Base Information

• Chemical Name: 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine
• CAS No.: 886227-21-0
• Molecular Formula: C₄₈H₅₆N₄O₇Si
• Molecular Weight: 829.081
• Mol file: 886227-21-0.mol

Synonyms:2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine

Chemical Property of 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine

There total 11 articles about 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine 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%

5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-3-deazaadenosine (176049-52-8) + triisopropylsilyl chloride (13154-24-0) → 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-3-deazaadenosine (886227-21-0) + 3'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-3-deazaadenosine

Guidance literature:

With pyridine; silver nitrate; In tetrahydrofuran; at 20 ℃; for 40h;

DOI:10.1021/ja0588454

Reference yield:

N-benzoyl-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine (176049-51-7) → 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-3-deazaadenosine (886227-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethylformamide dimethyl acetal; pyridine / 1.5 h / 20 °C

1.2: 62 percent / pyridine / 18 h / 20 °C

2.1: 60 percent / pyridine; AgNO₃ / tetrahydrofuran / 40 h / 20 °C

With pyridine; silver nitrate; N,N-dimethyl-formamide dimethyl acetal; In tetrahydrofuran;

DOI:10.1021/ja0588454

Reference yield:

5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile (886227-20-9) → 2'-O-triisopropylsilyl-5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-3-deazaadenosine (886227-21-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Pd(PhCN)2Cl₂; Et₃N / acetonitrile / 20 h / 110 °C

1.2: 50 percent / NH₃; methanol / 14 h / 120 °C

2.1: 79 percent / Amberlite IRA 900 fluoride-form / toluene / 6 h / Heating

3.1: chlorotrimethylsilane; pyridine / 0.83 h / 0 °C

3.2: pyridine / 3.5 h / 0 - 20 °C

3.3: 90 percent / aq. NH₃ / 3 h / 20 °C

4.1: N,N-dimethylformamide dimethyl acetal; pyridine / 1.5 h / 20 °C

4.2: 62 percent / pyridine / 18 h / 20 °C

5.1: 60 percent / pyridine; AgNO₃ / tetrahydrofuran / 40 h / 20 °C

With pyridine; bis(benzonitrile)palladium(II) dichloride; chloro-trimethyl-silane; Amberlite IRA 900 fluoride-form; silver nitrate; N,N-dimethyl-formamide dimethyl acetal; triethylamine; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1021/ja0588454

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-N⁶-benzoyl-3-deazaadenosine

triisopropylsilyl chloride

N-benzoyl-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine

5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile