(2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide

Base Information

• Chemical Name: (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide
• CAS No.: 360558-63-0
• Molecular Formula: C₂₆H₃₁BrFNO₄
• Molecular Weight: 520.439

Synonyms:(2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide

Chemical Property of (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide

Chemical Property:

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Technology Process of (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide

There total 9 articles about (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 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: 77.0%

2-((1R,2R,3S)-1-Bromomethyl-2-fluoro-3-nitromethyl-4-phenyl-butoxy)-tetrahydro-pyran (360558-61-8) + (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8) → (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide (360558-63-0)

Guidance literature:

2-((1R,2R,3S)-1-Bromomethyl-2-fluoro-3-nitromethyl-4-phenyl-butoxy)-tetrahydro-pyran; With potassium tert-butylate; In tert-butyl alcohol; at 23 ℃; for 0.0833333h;

With borax; potassium permanganate; sodium tetraborate; In water; tert-butyl alcohol; at 0 ℃; for 0.25h;

(1S,2R)-1-amino-2-indanol; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; Further stages.;

DOI:10.1021/ja010113y

Reference yield:

(R)-2-Fluoro-3-nitromethyl-4-phenyl-butyryl chloride → (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide (360558-63-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

3.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

4.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

5.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

5.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

5.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

With lithium borohydride; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; hexane; tert-butyl alcohol;

DOI:10.1021/ja010113y

Reference yield:

(R)-2-Fluoro-3-nitromethyl-4-phenyl-butyric acid → (2S,3R,4R)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide (360558-63-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (COCl)2; DMF / CH₂Cl₂ / 0 - 23 °C

2.1: 3.41 g / tetrahydrofuran; hexane / 2 h / 0 °C

3.1: 96 percent / glacial acetic acid; aq. HBr / 0.17 h / 0 °C

4.1: 29 percent / lithium borohydride / tetrahydrofuran / -100 - -78 °C

5.1: 96 percent / p-toluenesulfonic acid monohydrate / 13 h / 23 °C

6.1: t-BuOK / 2-methyl-propan-2-ol / 0.08 h / 23 °C

6.2: sodium tetraborate; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

6.3: 77 percent / 1-hydroxybenzotriazole; EDC*HCl; triethylamine / CH₂Cl₂

With lithium borohydride; oxalyl dichloride; potassium tert-butylate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja010113y

upstream raw materials:

2-((1R,2R,3S)-1-Bromomethyl-2-fluoro-3-nitromethyl-4-phenyl-butoxy)-tetrahydro-pyran

(1S,2R)-1-amino-2-indanol

(R)-1-Diazo-3-fluoro-4-nitromethyl-5-phenyl-pentan-2-one

(R)-1-Bromo-3-fluoro-4-nitromethyl-5-phenyl-pentan-2-one

Downstream raw materials:

(S)-1-[(3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2,5-dioxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

(S)-1-[(2S,3R,4S)-4-Benzyl-5-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-2-hydroxy-5-oxo-pentyl]-4-pyridin-3-ylmethyl-piperazine-2-carboxylic acid tert-butylamide

(2S,3R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-3-(S)-oxiranyl-propan-1-one

(2S,3R,4R)-2-Benzyl-5-bromo-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-fluoro-4-hydroxy-pentan-1-one

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