N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Base Information

• Chemical Name: N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine
• CAS No.: 1356151-97-7
• Molecular Formula: C₃₄H₄₁BrN₄O₉Si
• Molecular Weight: 757.71
• Mol file: 1356151-97-7.mol

Synonyms:N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Chemical Property of N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

There total 4 articles about N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine 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: 81.0%

N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-96-6) → N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-97-7)

Guidance literature:

With ammonia; In methanol; at 0 - 20 ℃; for 12h; Autoclave;

DOI:10.1021/jo202319f

Reference yield:

2',3'-O-isopropylidene-8-bromoinosine (23339-40-4) → N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

2.2: -78 - 20 °C

3.1: ammonia / methanol / 12 h / 0 - 20 °C / Autoclave

With 1H-imidazole; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo202319f

Reference yield:

8-bromo-2',3'-O-isopropylene adenosine (13089-45-7) → N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-97-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium nitrite / water; acetic acid / 16 h

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

3.2: -78 - 20 °C

4.1: ammonia / methanol / 12 h / 0 - 20 °C / Autoclave

With 1H-imidazole; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo202319f

upstream raw materials:

N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

2',3'-isopropylidene adenosine

8-bromo-2',3'-O-isopropylene adenosine

2',3'-O-isopropylidene-8-bromoinosine

Downstream raw materials:

N1-[2,3-O-isopropylidene-5-O-di(tert-butyl)phosphoryl-β-D-ribofuranosyl]-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

N1-[2,3-O-isopropylidene-5-O-di(tert-butyl)phosphoryl-β-D-ribofuranosyl]-5'-O-di(phenylthio)phosphoryl-2',3'-O-isopropylidene-8-bromoinosine

N1-(5-O-phosphoryl-β-D-ribofuranosyl)-5'-O-di(phenylthio)phosphoryl-8-bromoinosine

N1-(5-O-phosphoryl-β-D-ribofuranosyl)-5'-O-(phenylthio)phosphoryl-8-bromoinosine