(2S,3S,4S)-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,3S,4S)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide
• CAS No.: 360558-23-2
• Molecular Formula: C₂₆H₃₁BrFNO₄
• Molecular Weight: 520.439

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

There total 11 articles about (2S,3S,4S)-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:

(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,3S,4S)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid → (2S,3S,4S)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide (360558-23-2)

Guidance literature:

(2S,3S,4S)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 23 ℃; for 0.166667h;

(1S,2R)-1-amino-2-indanol; With triethylamine; In dichloromethane; at 23 ℃; for 5.5h; Further stages.;

DOI:10.1021/ja010113y

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (2S,3S,4S)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide (360558-23-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / p-TsOH*H₂O / CH₂Cl₂ / 23 h / 23 °C

2.1: t-BuOK / 2-methyl-propan-2-ol / 0.05 h / 23 °C

2.2: KMnO₄; Na₂B₄O₇ / H₂O; 2-methyl-propan-2-ol / 1 h / 23 °C

3.1: EDC*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0.17 h / 23 °C

3.2: 39.3 mg / Et₃N / CH₂Cl₂ / 5.5 h / 23 °C

With potassium tert-butylate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja010113y

Reference yield:

1-nitro-2-acetoxy-3-phenylpropane (62634-65-5) → (2S,3S,4S)-2-Benzyl-5-bromo-3-fluoro-4-(tetrahydro-pyran-2-yloxy)-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide (360558-23-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 73 percent / sodium carbonate / benzene / 4 h / Heating

2.1: LHMDS; LiCl / tetrahydrofuran; hexane / 1.3 h / -78 °C

2.2: 23 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.1: 88 percent / NaOH / 2-methyl-propan-2-ol; methanol; H₂O / 4 h / 75 °C

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

5.1: 55.2 mg / tetrahydrofuran; hexane / 2 h / 0 °C

6.1: 93 percent / aq. HBr; AcOH / 0.17 h / 0 °C

7.1: 75 percent / NaBH₄ / ethanol / 1.3 h / -78 °C

8.1: 93 percent / p-TsOH*H₂O / CH₂Cl₂ / 23 h / 23 °C

9.1: t-BuOK / 2-methyl-propan-2-ol / 0.05 h / 23 °C

9.2: KMnO₄; Na₂B₄O₇ / H₂O; 2-methyl-propan-2-ol / 1 h / 23 °C

10.1: EDC*HCl; 1-hydroxybenzotriazole / CH₂Cl₂ / 0.17 h / 23 °C

10.2: 39.3 mg / Et₃N / CH₂Cl₂ / 5.5 h / 23 °C

With sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen bromide; sodium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ja010113y

upstream raw materials:

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

3,4-dihydro-2H-pyran

1-nitro-2-acetoxy-3-phenylpropane

(E)-3-phenyl-1-nitroprop-1-ene

Downstream raw materials:

(S)-4-[(2R,3S,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]-3-tert-butylcarbamoyl-piperazine-1-carboxylic acid benzyl ester

(S)-1-[(2S,3S,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

(S)-1-[(2R,3S,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]-piperazine-2-carboxylic acid tert-butylamide

(S)-1-[(2R,3S,4S)-3-Fluoro-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide

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