(2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol

Base Information

• Chemical Name: (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol
• CAS No.: 169687-99-4
• Molecular Formula: C₂₀H₂₅N₉O₃
• Molecular Weight: 439.477
• Mol file: 169687-99-4.mol

Synonyms:(2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol

Chemical Property of (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol

There total 8 articles about (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol 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: 91.0%

9-((2R,3S,3aS,9aR)-3-Azido-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-N2-(4-butyl-phenyl)-9H-purine-2,6-diamine (169687-96-1) → (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol (169687-99-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 14h; Ambient temperature;

Reference yield:

2-(4-butyl-anilino)-adenosine (169687-92-7) → (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol (169687-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92.1 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

2: 79 percent / DMAP, Et₃N / pyridine / 3.5 h / Ambient temperature

3: 58 percent / LiN₃ / hexamethylphosphoric acid triamide / 2.5 h / Ambient temperature

4: 91 percent / TBAF / tetrahydrofuran / 14 h / Ambient temperature

With 1H-imidazole; dmap; lithium azide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;

Reference yield:

4-Butylaniline (104-13-2) → (2R,3S,4S,5R)-5-[6-Amino-2-(4-butyl-phenylamino)-purin-9-yl]-4-azido-2-hydroxymethyl-tetrahydro-furan-3-ol (169687-99-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 75.9 percent / methanol / 4 h / 95 °C

2: 1.) Et₄NCl, N,N-dimethylaniline, POCl₃, 2.) NH₃/MeOH / 1.) MeCN, 80 deg C, 1 h, 2.) 120 deg C, 5 h

3: 92.1 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

4: 79 percent / DMAP, Et₃N / pyridine / 3.5 h / Ambient temperature

5: 58 percent / LiN₃ / hexamethylphosphoric acid triamide / 2.5 h / Ambient temperature

6: 91 percent / TBAF / tetrahydrofuran / 14 h / Ambient temperature

With 1H-imidazole; methanol; dmap; lithium azide; tetraethylammonium chloride; tetrabutyl ammonium fluoride; ammonia; N,N-dimethyl-aniline; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;

upstream raw materials:

9-((2R,3S,3aS,9aR)-3-Azido-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-N²-(4-butyl-phenyl)-9H-purine-2,6-diamine

2-(4-butyl-anilino)-adenosine

4-Butylaniline

6-amino-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine