5'-S-acetyl-N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine

Base Information

• Chemical Name: 5'-S-acetyl-N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine
• CAS No.: 172161-67-0
• Molecular Formula: C₂₄H₃₃N₃O₅SSi
• Molecular Weight: 503.695

Synonyms:5'-S-acetyl-N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine

Chemical Property of 5'-S-acetyl-N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine

Chemical Property:

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Technology Process of 5'-S-acetyl-N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine

There total 2 articles about 5'-S-acetyl-N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine 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: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5'-S-acetyl-N4-benzoyl-2',5'-dideoxy-5'-thiocytidine (172161-64-7) → 5'-S-acetyl-N4-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine (172161-67-0)

Guidance literature:

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

Reference yield:

N4-benzoyl-2'-deoxycytidine (4836-13-9) → 5'-S-acetyl-N4-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine (172161-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 - 20 °C

2: 92 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: 56.0%

5'-S-acetyl-N4-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine (172161-67-0) → N4-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine (172161-52-3)

Guidance literature:

With sodium hydroxide; In methanol;

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

upstream raw materials:

tert-butyldimethylsilyl chloride

5'-S-acetyl-N⁴-benzoyl-2',5'-dideoxy-5'-thiocytidine

N₄-benzoyl-2'-deoxycytidine

Downstream raw materials:

N⁴-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thiocytidine

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