(S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide

Base Information

• Chemical Name: (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide
• CAS No.: 76398-88-4
• Molecular Formula: C₂₃H₃₀N₈O₅
• Molecular Weight: 498.542
• Mol file: 76398-88-4.mol

Synonyms:(S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide

Chemical Property of (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide

There total 5 articles about (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide 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: 88.0%

6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine (76381-69-6) → (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide (76398-88-4)

Guidance literature:

With trifluoroacetic acid; for 0.0833333h; Ambient temperature;

DOI:10.1021/jm00135a013

Reference yield:

4-nitro-3-phenyl-L-alanine (949-99-5) → (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide (76398-88-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 44 percent / magnesium hydroxide / H₂O; dioxane / 20 h / 40 °C

2: 70.5 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

3: 88.3 percent / H₂, glacial CH₃COOH / 10percent Pd/C / 4 h / 760 Torr / Ambient temperature

4: 69.3 percent / dioxane / 72 h / Ambient temperature

5: 88 percent / trifluoroacetic acid / 0.08 h / Ambient temperature

With magnesium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00135a013

Reference yield:

Boc-Phe(p-NO2)-OH (33305-77-0) → (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide (76398-88-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 70.5 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature

2: 88.3 percent / H₂, glacial CH₃COOH / 10percent Pd/C / 4 h / 760 Torr / Ambient temperature

3: 69.3 percent / dioxane / 72 h / Ambient temperature

4: 88 percent / trifluoroacetic acid / 0.08 h / Ambient temperature

With 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00135a013

upstream raw materials:

6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine

4-nitro-3-phenyl-L-alanine

Boc-Phe(p-NO₂)-OH

6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine