N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine

Base Information

• Chemical Name: N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine
• CAS No.: 889126-09-4
• Molecular Formula: C₁₇H₁₇IN₈O₃
• Molecular Weight: 508.278
• Mol file: 889126-09-4.mol

Synonyms:N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine

Chemical Property of N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine

There total 8 articles about N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine 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: 86.0%

3-iodobenzylamine hydrochloride (3718-88-5) + 2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose (889126-06-1) → N6-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine (889126-09-4)

Guidance literature:

3-iodobenzylamine hydrochloride; 2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose; With triethylamine; In ethanol; at 50 ℃; for 18h;

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jm050968b

Reference yield: 18.0%

Acetic acid (3R,4R,5S)-2-acetoxy-4-azido-5-p-tolyloxymethyl-tetrahydro-furan-3-yl ester + (3-iodo-benzyl)-(9-trimethylsilanyl-9H-purin-6-yl)-amine → N6-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine (889126-09-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 83 ℃; for 6.5h;

DOI:10.1021/jm010232o

Reference yield:

1,2,5-tri-O-acetyl-3-azido-3-deoxy-D-ribofuranose (179530-74-6) → N6-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine (889126-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSOTf / 1,2-dichloro-ethane / 0 - 60 °C

2: Et₃N / ethanol

3: NaOMe; MeOH

With methanol; sodium methylate; triethylamine; trimethylsilyl trifluoromethanesulfonate; In ethanol; 1,2-dichloro-ethane;

DOI:10.1081/NCN-200060079

upstream raw materials:

3-iodobenzylamine hydrochloride

2,5-di-O-acetyl-3-azido-1-(6-chloropurin-9-yl)-β-D-1,3-dideoxyribofuranose

1,2,5-tri-O-acetyl-3-azido-3-deoxy-D-ribofuranose

5-O-acetyl-3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Downstream raw materials:

N⁶-(3-iodobenzyl)-9-(3-amino-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine

N⁶-(3-iodobenzyl)-9-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine