(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester

Base Information

• Chemical Name: (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester
• CAS No.: 1394050-56-6
• Molecular Formula: C₂₈H₃₁NO₅
• Molecular Weight: 461.558
• Mol file: 1394050-56-6.mol

Synonyms:(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester

Chemical Property of (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester

There total 5 articles about (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester 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:

C33H39NO7 → (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester (1394050-56-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

Reference yield:

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (128779-47-5) → (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester (1394050-56-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 9 h / -5 °C / Inert atmosphere

2.1: acetic acid / dichloromethane / 0.5 h / -5 °C / Inert atmosphere

2.2: 2 h / -5 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 23 °C / Inert atmosphere

4.1: samarium diiodide / water; tetrahydrofuran / 0.25 h / Inert atmosphere

5.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 0.25 h / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; samarium diiodide; potassium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

[(R)-1-biphenyl-4-ylmethyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxoethyl]carbamic acid t-butyl ester (1383026-37-6) → (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid benzyloxycarbonylmethyl ester (1394050-56-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic acid / dichloromethane / 0.5 h / -5 °C / Inert atmosphere

1.2: 2 h / -5 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 23 °C / Inert atmosphere

3.1: samarium diiodide / water; tetrahydrofuran / 0.25 h / Inert atmosphere

4.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 0.25 h / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: hydrogenchloride / 1,4-dioxane; acetonitrile / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; samarium diiodide; potassium carbonate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

[(R)-1-biphenyl-4-ylmethyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxoethyl]carbamic acid t-butyl ester

[(S)-2-biphenyl-4-yl-1-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)ethyl]carbamic acid t-butyl ester

[(R)-1-(biphenyl-4-yl)-methyl-2-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid t-butyl ester

Downstream raw materials:

(2S,4R)-5-Biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid benzyloxycarbonylmethyl ester