(5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine

Base Information

• Chemical Name: (5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine
• CAS No.: 222736-09-6
• Molecular Formula: C₄₄H₄₇N₅O₆Si
• Molecular Weight: 769.973
• Mol file: 222736-09-6.mol

Synonyms:(5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine

Chemical Property of (5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine

There total 4 articles about (5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine 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:

(5?'S)-N6-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine (211919-88-9) → (5'R)-N6-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine (222736-09-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.913 g / (C₂H₅)3N / pyridine; CH₂Cl₂ / 3 h / 20 °C

2: 0.4 g / KO₂; 18-C-6 crown ether / dimethylsulfoxide; 1,2-dimethoxy-ethane / 9 h / 20 °C

3: 0.136 g / pyridine / 4 h / 80 °C

With 18-crown-6 ether; triethylamine; In pyridine; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/tx9802668

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) + (5?'R)-N6-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine (222736-08-5) → (5'R)-N6-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine (222736-09-6)

Guidance literature:

With pyridine; at 80 ℃; for 4h;

DOI:10.1080/07328319908044708

Reference yield:

(5'S)-N6-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-mesyl-5',8-cyclo-2'-deoxyadenosine → (5'R)-N6-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine (222736-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.4 g / KO₂; 18-C-6 crown ether / dimethylsulfoxide; 1,2-dimethoxy-ethane / 9 h / 20 °C

2: 0.136 g / pyridine / 4 h / 80 °C

With 18-crown-6 ether; In pyridine; 1,2-dimethoxyethane; dimethyl sulfoxide;

DOI:10.1021/tx9802668

upstream raw materials:

4,4'-dimethoxytrityl chloride

(5?'R)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine

(5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine

C₂₄H₃₁N₅O₆SSi

Downstream raw materials:

(5'R)-N₆-benzoyl-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine