5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine

Base Information

• Chemical Name: 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine
• CAS No.: 484024-76-2
• Molecular Formula: C₂₃H₃₀FN₅O₄SSi
• Molecular Weight: 519.672

Synonyms:5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine

Chemical Property of 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine

Chemical Property:

Purity/Quality:

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Technology Process of 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine

There total 3 articles about 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)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: 74.0%

phenylcarbonochloridothioate (1005-56-7) + 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoroadenosine (484024-74-0) → 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine (484024-76-2)

Guidance literature:

With dmap; In acetonitrile; for 5h;

DOI:10.1021/jo020428b

Reference yield:

(2R,3S,4S,5R)-2-(6-amino-9H-purine-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol (75059-22-2) → 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine (484024-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / imidazole / dimethylformamide

2: 74 percent / DMAP / acetonitrile / 5 h

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo020428b

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoro-2'-O-(phenoxythiocarbonyl)adenosine (484024-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / imidazole / dimethylformamide

2: 74 percent / DMAP / acetonitrile / 5 h

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo020428b

upstream raw materials:

phenylcarbonochloridothioate

5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-fluoroadenosine

(2R,3S,4S,5R)-2-(6-amino-9H-purine-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol

tert-butyldimethylsilyl chloride

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