O⁶-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine

Base Information

• Chemical Name: O⁶-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine
• CAS No.: 1384519-90-7
• Molecular Formula: C₄₂H₆₂N₁₀O₅Si₃
• Molecular Weight: 871.275

Synonyms:O⁶-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine

Chemical Property of O⁶-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine

Chemical Property:

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Technology Process of O⁶-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine

There total 6 articles about O⁶-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine 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: 55.0%

2-[(4-phenyl)-1,2,3-triazol-1H-yl]-2′,3′-5′-tri-O-(tert-butyldimethylsilyl)inosine (1398237-71-2) + (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (56602-33-6) → O6-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine (1384519-90-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 2 ℃; for 24h; Inert atmosphere;

Reference yield: 55.0%

2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine (1398237-71-2) + (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (56602-33-6) → O6-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine (1384519-90-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo300628y

Reference yield:

2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine (72409-24-6) → O6-(1-benzotriazol-1H-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)inosine (1384519-90-7)

Guidance literature:

Multi-step reaction with 6 steps

1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C

2: caesium carbonate / 2 h / 20 °C / Inert atmosphere

3: tert.-butylnitrite; trimethylsilylazide / dichloromethane / 25 h / -20 - 20 °C

4: copper(l) chloride / water; tert-butyl alcohol / 20 °C / Inert atmosphere

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium benzenesulfonate / tetrahydrofuran; methanol / 2 h / 20 °C

6: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tert.-butylnitrite; trimethylsilylazide; sodium benzenesulfonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo300628y

upstream raw materials:

2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine

O⁶-(benzotriazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine

O⁶-allyl-2',3',5'-tri-O-(tert-butyldimethylsilyl)guanosine

O⁶-allyl-2-azido-2',3',5'-tri-O-(tert-butyldimethylsily)inosine

Downstream raw materials:

6-(morpholin-4-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-9-[2',3',5'-tri-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine

6-(morpholin-4-yl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-9-(β-D-ribofuranosyl)purine

6-(N-benzyl)-2-[4-(phenyl)-1,2,3-triazol-1H-yl]adenosine

6-(N-benzyl)-2-(4-phenyl-1,2,3-triazol-1H-yl)-2',3',5'-tri-O-(tert-butyldimethylsilyl)adenosine

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