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

Base Information

• Chemical Name: 5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine
• CAS No.: 1256503-22-6
• Molecular Formula: C₂₉H₃₃BrN₄O₅Si
• Molecular Weight: 625.594
• Mol file: 1256503-22-6.mol

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

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

There total 2 articles about 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%

tert-butylchlorodiphenylsilane (58479-61-1) + 2',3'-O-isopropylidene-8-bromoinosine (23339-40-4) → 5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1256503-22-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c0ob00090f

Reference yield:

2',3'-isopropylidene adenosine (362-75-4) → 5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1256503-22-6)

Guidance literature:

Multi-step reaction with 3 steps

1: disodium hydrogenphosphate; bromine / 1,4-dioxane; water / 16 h / Darkness

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

3: 1H-imidazole / N,N-dimethyl-formamide / 16 h

With 1H-imidazole; disodium hydrogenphosphate; bromine; sodium nitrite; In 1,4-dioxane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo202319f

Reference yield: 90.0%

5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1256503-22-6) + 1,2,3,5-tetraacetylribose (13035-61-5) → N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine (1356151-96-6)

Guidance literature:

5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.5h;

1,2,3,5-tetraacetylribose; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; stereoselective reaction;

DOI:10.1021/jo202319f

upstream raw materials:

tert-butylchlorodiphenylsilane

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

2',3'-isopropylidene adenosine

Downstream raw materials:

N₁-[(5''-acetoxyethoxy)methyl]-5'-O-TBDPS-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