7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Base Information

• Chemical Name: 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
• CAS No.: 287101-38-6
• Molecular Formula: C₂₅H₂₃N₃O₇
• Molecular Weight: 477.474
• Mol file: 287101-38-6.mol

Synonyms:7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Chemical Property of 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

There total 2 articles about 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 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: 93.0%

phenylacetylene (536-74-3) + 7-iodo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine (287101-37-5) → 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine (287101-38-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 90 ℃; for 2h;

DOI:10.1021/jf0000225

Reference yield:

7-amino-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-b]pyridine → 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine (287101-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / isoamyl nitrite; CH₂I₂ / 2 h / 90 °C / Irradiation

2: 93 percent / (PPh₃)2PdCl₂; CuI; Et₃N / acetonitrile / 2 h / 90 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diiodomethane; triethylamine; isopentyl nitrite; In acetonitrile; 1: Iodination / 2: Alkylation;

DOI:10.1021/jf0000225

Reference yield: 89.0%

7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine (287101-38-6) → 7-phenylethynyl-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine (287101-39-7)

Guidance literature:

With ammonia; In methanol; at 4 ℃; for 16h;

DOI:10.1021/jf0000225

upstream raw materials:

phenylacetylene

7-iodo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Downstream raw materials:

7-phenylethynyl-3-(β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine