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

Base Information

• Chemical Name: 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
• CAS No.: 1356152-01-6
• Molecular Formula: C₄₁H₅₃BrN₄O₁₃P₂S₂
• Molecular Weight: 1015.87
• Mol file: 1356152-01-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 100.0%

N1-[2,3-O-isopropylidene-5-O-di(tert-butyl)phosphoryl-β-D-ribofuranosyl]-2',3'-O-isopropylidene-8-bromoinosine (1356152-00-5) + cyclohexylammonium S,S-diphenyl phosphorodithioate (67941-87-1) → 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 (1356152-01-6)

Guidance literature:

With 2,4,6-triisopropylphenylsulfonyl chloride; 5-Phenyl-1H-tetrazole; In pyridine; at 20 ℃; for 5h;

DOI:10.1021/jo202319f

Reference yield:

2',3'-O-isopropylidene-8-bromoinosine (23339-40-4) → 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 (1356152-01-6)

Guidance literature:

Multi-step reaction with 8 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

4.1: toluene-4-sulfonic acid / acetone / 0.5 h

4.2: DOWEX H+ resin / 0.5 h

5.1: 5-Phenyl-1H-tetrazole / dichloromethane / 2 h

6.1: dihydrogen peroxide; triethylamine / dichloromethane / 0 - 20 °C

7.1: tetrabutyl ammonium fluoride; acetic acid / N,N-dimethyl-formamide / 0 - 20 °C

8.1: 2,4,6-triisopropylphenylsulfonyl chloride; 5-Phenyl-1H-tetrazole / pyridine / 5 h / 20 °C

With 1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; 5-Phenyl-1H-tetrazole; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo202319f

Reference yield:

5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1256503-22-6) → 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 (1356152-01-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

1.2: -78 - 20 °C

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

3.1: toluene-4-sulfonic acid / acetone / 0.5 h

3.2: DOWEX H+ resin / 0.5 h

4.1: 5-Phenyl-1H-tetrazole / dichloromethane / 2 h

5.1: dihydrogen peroxide; triethylamine / dichloromethane / 0 - 20 °C

6.1: tetrabutyl ammonium fluoride; acetic acid / N,N-dimethyl-formamide / 0 - 20 °C

7.1: 2,4,6-triisopropylphenylsulfonyl chloride; 5-Phenyl-1H-tetrazole / pyridine / 5 h / 20 °C

With 2,4,6-triisopropylphenylsulfonyl chloride; 5-Phenyl-1H-tetrazole; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo202319f

upstream raw materials:

5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

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

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

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

Downstream raw materials:

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