5'-O-(4,4'-dimethoxytrityl)-N⁶-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-N⁶-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine
• CAS No.: 661471-87-0
• Molecular Formula: C₄₂H₅₅N₅O₇Si
• Molecular Weight: 770.014

Synonyms:5'-O-(4,4'-dimethoxytrityl)-N⁶-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine

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

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-N⁶-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine

There total 7 articles about 5'-O-(4,4'-dimethoxytrityl)-N⁶-methyl-2'-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: 23.0%

chloromethoxy-triisopropyl-silane (217300-17-9) + 5'-O-(4,4'-dimethoxytrityl)-N6-methyladenosine (588698-71-9) → 5'-O-(4,4'-dimethoxytrityl)-N6-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine (661471-87-0) + 5'-O-(4,4'-dimethoxytrityl)-N6-methyl-3'-O-[[(triisopropylsilyl)oxy]methyl]adenosine

Guidance literature:

5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine; With di-tert-butyltin dichloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 70 ℃; for 15h;

chloromethoxy-triisopropyl-silane; In 1,2-dichloro-ethane; at 20 ℃; for 1h;

DOI:10.1007/s00706-003-0592-1

Reference yield:

9-[3',5'-di-O-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-ribofuranosyl]-6-(3-nitro-1H-1,2,4-triazol-1-yl)purine (672298-94-1) → 5'-O-(4,4'-dimethoxytrityl)-N6-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine (661471-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 3 h / 20 °C

2: 120 mg / pyridine / 3 h / 20 °C

With pyridine; In ethanol;

DOI:10.1002/hlca.200590209

Reference yield:

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) → 5'-O-(4,4'-dimethoxytrityl)-N6-methyl-2'-O-[[(triisopropylsilyl)oxy]methyl]adenosine (661471-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ethanol; H₂O / 12 h / 20 °C

2.1: 1.0 g / pyridine / 20 °C / overnight

3.1: i-Pr₂EtN; tert-Bu₂SnCl₂ / 1,2-dichloro-ethane / 15 h / 70 °C

3.2: 23 percent / 1,2-dichloro-ethane / 1 h / 20 °C

With di-tert-butyltin dichloride; N-ethyl-N,N-diisopropylamine; In pyridine; ethanol; water; 1,2-dichloro-ethane;

DOI:10.1007/s00706-003-0592-1

upstream raw materials:

chloromethoxy-triisopropyl-silane

5'-O-(4,4'-dimethoxytrityl)-N⁶-methyladenosine

4,4'-dimethoxytrityl chloride

9-[3',5'-di-O-acetyl-2'-O-{[(triisopropylsilyl)oxy]methyl}-β-D-ribofuranosyl]-6-(3-nitro-1H-1,2,4-triazol-1-yl)purine

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