β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine

Base Information

• Chemical Name: β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine
• CAS No.: 221156-13-4
• Molecular Formula: C₃₁H₃₄FN₃O₃SeSi
• Molecular Weight: 622.673

Synonyms:β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine

Chemical Property of β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine

There total 2 articles about β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine 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:

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose (149656-26-8) + 5-Fluoro-1-trimethylsilanyl-4-(trimethylsilanyl-amino)-1H-pyrimidin-2-one (168332-11-4) → β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine (221156-13-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 5 - 20 ℃; for 0.5h; Yield given;

DOI:10.1021/jm980510s

Reference yield:

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose (149656-26-8) + 5-Fluoro-1-trimethylsilanyl-4-(trimethylsilanyl-amino)-1H-pyrimidin-2-one (168332-11-4) → α-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine (221156-14-5) + β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine (221156-13-4)

Guidance literature:

With tin(IV) chloride; Yield given; Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, RT, 15 min, 2.) CH₂Cl₂, 0 deg C, 2 h;

DOI:10.1021/jm980510s

Reference yield: 86.0%

β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine (221156-13-4) → β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (221156-15-6)

Guidance literature:

With pyridine; dihydrogen peroxide; In dichloromethane; at 0 - 20 ℃; for 0.833333h;

DOI:10.1021/jm980510s

upstream raw materials:

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

5-Fluoro-1-trimethylsilanyl-4-(trimethylsilanyl-amino)-1H-pyrimidin-2-one

Downstream raw materials:

β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

β-D-N⁴-acetyl-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

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