5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine

Base Information

• Chemical Name: 5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine
• CAS No.: 318246-77-4
• Molecular Formula: C₃₇H₄₃FN₂O₆SSi
• Molecular Weight: 690.908
• Mol file: 318246-77-4.mol

Synonyms:5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine

Chemical Property of 5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine

There total 1 articles about 5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine 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:

3-tert-butylphenyl chlorothionoformate (97986-06-6) + 1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (110497-15-9) → 5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine (318246-77-4)

Guidance literature:

DOI:10.1021/jo001699u

Reference yield: 57.0%

(2-phenylvinyl)tributylstannane (66680-87-3,66680-88-4,79159-76-5) + 5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine (318246-77-4) → 5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-2'-β-fluoro-3'-C-(2-phenylethenyl)-5-methyluridine (337980-10-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; for 2h; Heating;

DOI:10.1021/jo001699u

Reference yield:

5'-O-(tert-butyldiphenylsilyl)-3'-O-(3-tert-butylphenoxythiocarbonyl)-2'-deoxy-2'-β-fluoro-5-methyluridine (318246-77-4) → 2',3'-dideoxy-2'-β-fluoro-5'-O-(4-methoxytrityl)-3'-C-methyl-5-methyluridine

Guidance literature:

Multi-step reaction with 7 steps

1.1: 57 percent / AIBN / benzene / 2 h / Heating

2.1: OsO₄; H₂O; N-methylmorpholine oxide / dioxane / 20 °C

2.2: NaIO₄ / H₂O; dioxane / 0 - 20 °C

3.1: 1.77 g / NaBH₄ / ethanol; H₂O / 2 h / 20 °C

4.1: 92 percent / methyl triphenoxyphosphonium iodide; 2,6-lutidine / dimethylformamide / 0 - 20 °C

5.1: 92 percent / triethylamine trifluoride / tetrahydrofuran / 20 °C

6.1: 88 percent / diisopropylethylamine / ethyl acetate; tetrahydrofuran / 20 °C

7.1: bis(trimethylsilyl)phosphonite; diisopropylethylamine / CH₂Cl₂ / 20 °C

7.2: 43 percent / MeOH / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); bis(trimethylsilyl) phosphonate; triethylamine trifluoride; methyltriphenoxyphosphonium iodide; water; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene; 7.1: Arbuzov reaction;

DOI:10.1021/jo001699u

upstream raw materials:

3-tert-butylphenyl chlorothionoformate

1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-2'-β-fluoro-3'-C-(2-phenylethenyl)-5-methyluridine

5'-O-(tert-butydiphenylsilyl)-2',3'-dideoxy-2'-β-fluoro-3'-C-(iodomethyl)-5-methyluridine

2',3'-dideoxy-2'-β-fluoro-3'-C-(iodomethyl)-5'-O-(4-methoxytrityl)-5-methyluridine

2',3'-dideoxy-5'-O-(4,4'-dimethoxytrityl)-2'-β-fluoro-3'-C-(iodomethyl)-5-methyluridine