5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine

Base Information

• Chemical Name: 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine
• CAS No.: 470699-93-5
• Molecular Formula: C₂₃H₂₇N₅O₈
• Molecular Weight: 501.496
• Mol file: 470699-93-5.mol

Synonyms:5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine

Chemical Property of 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine

There total 1 articles about 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine 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: 95.0%

2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2-N,3-N-bis(tert-butyloxycarbonyl)-2'-deoxy-4'α-methoxycarbonylguanosine → 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine (470699-93-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(02)00557-4

Reference yield: 60.0%

2-(2-iodophenyl)-1-ethanethiol (177748-62-8) + 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine (470699-93-5) → 5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-2'-deoxy-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}guanosine (470699-94-6)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In tetrahydrofuran; dichloromethane; for 2h; Heating;

DOI:10.1016/S0040-4020(02)00557-4

Reference yield:

5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxyguanosine (470699-93-5) → 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}guanosine (470700-03-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / BOP-Cl; triethylamine / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

2: DMAP / CH₂Cl₂ / 0 °C

3: iodine; 2,6-lutidine / CH₂Cl₂; tetrahydrofuran; H₂O

4: 85 percent / TMSOTf / CH₂Cl₂ / 0.83 h / 0 °C

With 2,6-dimethylpyridine; dmap; trimethylsilyl trifluoromethanesulfonate; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(02)00557-4

Downstream raw materials:

5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-2'-deoxy-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}guanosine

5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}guanosine

5'-O-benzyl-2-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}guanosine