(Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N³-methyl-4-thiothymidine 3'-(methylphosphonate)

Base Information

• Chemical Name: (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N³-methyl-4-thiothymidine 3'-(methylphosphonate)
• CAS No.: 163436-89-3
• Molecular Formula: C₅₄H₆₇N₄O₁₀PSSi₂
• Molecular Weight: 1051.36
• Mol file: 163436-89-3.mol

Synonyms:

Chemical Property of (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N³-methyl-4-thiothymidine 3'-(methylphosphonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N³-methyl-4-thiothymidine 3'-(methylphosphonate)

There total 10 articles about (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N³-methyl-4-thiothymidine 3'-(methylphosphonate) 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: 33.0%

3'-O-(tert-Butyldiphenylsilyl)-N3-methyl-4-thiothymidine (163295-92-9) + 5'-O-(tert-Butyldiphenylsilyl)thymidine 3'-(methylphosphonate) triethylammonium salt → (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N3-methyl-4-thiothymidine 3'-(methylphosphonate) (163436-89-3) + (Rp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N3-methyl-4-thiothymidine 3'-(methylphosphonate) (163295-94-1)

Guidance literature:

With 4-methoxypyridine N-oxide; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; In pyridine; for 1h; Ambient temperature;

DOI:10.1021/jo00103a018

Reference yield:

3-methylthymidine (958-74-7) → (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N3-methyl-4-thiothymidine 3'-(methylphosphonate) (163436-89-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / pyridine / 1 h / Ambient temperature

2: Lawesson reagent / dioxane / 12 h / Heating

3: NaOMe / methanol / 0.5 h / Heating

4: 82 percent / pyridine, Et₃N / 16 h / Ambient temperature

5: imidazole / dimethylformamide / 3 h / Ambient temperature

6: TsOH*H₂O / CHCl₃; methanol / 0.33 h / Ambient temperature

7: 38 percent / 4-methoxypyridine 1-oxide, 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphinane / pyridine / 1 h / Ambient temperature

With Lawessons reagent; pyridine; 1H-imidazole; 4-methoxypyridine N-oxide; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; sodium methylate; toluene-4-sulfonic acid; triethylamine; In 1,4-dioxane; pyridine; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo00103a018

Reference yield:

N-3-methyl-4-thiothymidine (144874-47-5) → (Sp)-5'-O-(tert-Butyldiphenylsilyl)thymidylyl-(3'->5')-3'-O-(ter-butyldiphenylsilyl)-N3-methyl-4-thiothymidine 3'-(methylphosphonate) (163436-89-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / pyridine, Et₃N / 16 h / Ambient temperature

2: imidazole / dimethylformamide / 3 h / Ambient temperature

3: TsOH*H₂O / CHCl₃; methanol / 0.33 h / Ambient temperature

4: 38 percent / 4-methoxypyridine 1-oxide, 2-chloro-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphinane / pyridine / 1 h / Ambient temperature

With pyridine; 1H-imidazole; 4-methoxypyridine N-oxide; 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide; toluene-4-sulfonic acid; triethylamine; In pyridine; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo00103a018

upstream raw materials:

3'-O-(tert-Butyldiphenylsilyl)-N³-methyl-4-thiothymidine

3-methylthymidine

N-3-methyl-4-thiothymidine

5'-O-tert-butyldiphenylsilylthymidine

Downstream raw materials:

(Sp)-Thymidylyl-(3'->5')-methyl-4-thiothymidine 3'-(methylphosphonate)