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

Base Information

• Chemical Name: N⁶-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5',6'-epoxy-5'-methyladenosine
• CAS No.: 331822-83-4
• Molecular Formula: C₂₄H₃₁N₅O₄Si
• Molecular Weight: 481.627

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

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

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

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

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',6'-epoxy-5'-methyladenosine (331822-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2M sodium hexamethyldisilazide / tetrahydrofuran / 1.5 h

1.2: 70 percent / tetrahydrofuran / 16 h / -78 - 20 °C

2.1: 30 percent / 0.14M dimethyldioxirane / acetone; CH₂Cl₂ / 60 h / 20 °C

With sodium hexamethyldisilazane; 3,3-dimethyldioxirane; In tetrahydrofuran; dichloromethane; acetone;

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

Reference yield: 62.0%

n-propylmagnesium bromide (927-77-5) + N6-benzoyl-3'-O-[(tert-butyl)dimethylsilyl]-2',5'-dideoxy-5',6'-epoxy-5'-methyladenosine (331822-83-4) → N6-benzoyl-5'-butyl-3'-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; at -40 - -18 ℃; for 2.5h;

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

upstream raw materials:

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

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

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