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

Base Information

• Chemical Name: N1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine
• CAS No.: 1356151-98-8
• Molecular Formula: C₃₇H₄₅BrN₄O₉Si
• Molecular Weight: 797.775
• Mol file: 1356151-98-8.mol

Synonyms:

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

There total 5 articles about N1-(2,3-O-isopropylidene-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: 99.0%

N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-97-7) + 2,2-dimethoxy-propane (77-76-9) → N1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-98-8)

Guidance literature:

N1-(β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine; 2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In acetone; for 0.5h;

In methanol; for 0.5h;

DOI:10.1021/jo202319f

Reference yield:

2',3'-O-isopropylidene-8-bromoinosine (23339-40-4) → N1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-98-8)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; ammonia; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo202319f

Reference yield:

N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-96-6) → N1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-98-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.2: DOWEX H+ resin / 0.5 h

With ammonia; toluene-4-sulfonic acid; In methanol; acetone;

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

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

2,2-dimethoxy-propane

2',3'-isopropylidene adenosine

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