5'-S-acetyl-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

Base Information

• Chemical Name: 5'-S-acetyl-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine
• CAS No.: 172161-66-9
• Molecular Formula: C₂₅H₃₃N₅O₄SSi
• Molecular Weight: 527.72

Synonyms:5'-S-acetyl-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

Chemical Property of 5'-S-acetyl-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

Chemical Property:

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Technology Process of 5'-S-acetyl-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

There total 2 articles about 5'-S-acetyl-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine 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: 91.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-S-acetyl-N6-benzoyl-2',5'-dideoxy-5'-thioadenosine (172161-63-6) → 5'-S-acetyl-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (172161-66-9)

Guidance literature:

DOI:10.1016/00404-0399(50)1393-V

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → 5'-S-acetyl-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (172161-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 - 20 °C

2: 91 percent / imidazole / dimethylformamide / 20 h / 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Mitsunobu coupling / 2: silylation;

DOI:10.1139/cjc-77-8-1410

Reference yield: 52.0%

5'-S-acetyl-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (172161-66-9) → N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine (172161-51-2)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/00404-0399(50)1393-V

upstream raw materials:

tert-butyldimethylsilyl chloride

5'-S-acetyl-N⁶-benzoyl-2',5'-dideoxy-5'-thioadenosine

N₆-benzoyl-2'-deoxyadenosine

Downstream raw materials:

N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

5'-S-acetyl-3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-N⁶-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine

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