N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine

Base Information

• Chemical Name: N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine
• CAS No.: 331822-82-3
• Molecular Formula: C₂₄H₃₁N₅O₃Si
• Molecular Weight: 465.627

Synonyms:N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine

Chemical Property of N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine

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Technology Process of N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine

There total 1 articles about N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine 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: 70.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 5'-aldehyde-2'-deoxy-6-N-benzoyl-3'-O-tertbutyldimethylsilyl adenosine (167700-45-0) → N6-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine (331822-82-3)

Guidance literature:

Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; for 1.5h;

5'-aldehyde-2'-deoxy-6-N-benzoyl-3'-O-tertbutyldimethylsilyl adenosine; In tetrahydrofuran; at -78 - 20 ℃; for 16h;

DOI:10.1002/1522-2675(20010131)84:1<87::AID-HLCA87>3.0.CO;2-1

Reference yield: 30.0%

N6-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine (331822-82-3) → N6-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5',6'-epoxy-5'-methyladenosine (331822-83-4)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 20 ℃; for 60h;

DOI:10.1002/1522-2675(20010131)84:1<87::AID-HLCA87>3.0.CO;2-1

Reference yield:

N6-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5'-methylideneadenosine (331822-82-3) → N6-benzoyl-5'-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / 0.14M dimethyldioxirane / acetone; CH₂Cl₂ / 60 h / 20 °C

2: 62 percent / CuI / tetrahydrofuran / 2.5 h / -40 - -18 °C

With copper(l) iodide; 3,3-dimethyldioxirane; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/1522-2675(20010131)84:1<87::AID-HLCA87>3.0.CO;2-1

upstream raw materials:

Methyltriphenylphosphonium bromide

5'-aldehyde-2'-deoxy-6-N-benzoyl-3'-O-tertbutyldimethylsilyl adenosine

Downstream raw materials:

N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5',6'-epoxy-5'-methyladenosine

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