(2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid

Base Information

• Chemical Name: (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid
• CAS No.: 1445984-59-7
• Molecular Formula: C₃₉H₅₃Cl₂N₅O₁₀S
• Molecular Weight: 854.849

Synonyms:(2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid

Chemical Property of (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid

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Technology Process of (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid

There total 15 articles about (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid 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: 71.0%

methyl (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoate → (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid (1445984-59-7)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/acs.jmedchem.8b00308

Reference yield:

1-cyclopropyl-4-[[(4R)-1,3-thiazolidin-4-yl]carbonyl]-1,2,3,4-tetrahydroquinoxaline (1445985-48-7) → (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid (1445984-59-7)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / N,N-dimethyl-formamide / 60 °C

2: lithium hydroxide monohydrate; water / tetrahydrofuran / 6 h

3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 30 °C

4: triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C

5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

With dmap; lithium hydroxide monohydrate; water; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.8b00308

Reference yield:

2,5-dichloro-4-formylphenyl trilluoromethanesulfonate (381229-84-1) → (2S)-2-[5-(2,5-dichloro-4-[[(4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidin-3-yl]methyl]phenyl)pentanamido]-4-[methyl[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl]butanoic acid (1445984-59-7)

Guidance literature:

Multi-step reaction with 10 steps

1: N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide

2: hydrogen; rhodium contaminated with carbon / ethyl acetate

3: sodium tetrahydroborate / methanol / 2 h / 0 - 5 °C

4: triphenylphosphine; N-Bromosuccinimide / dichloromethane; tetrahydrofuran / 1 h / 0 °C

5: potassium carbonate / N,N-dimethyl-formamide / 60 °C

6: lithium hydroxide monohydrate; water / tetrahydrofuran / 6 h

7: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 30 °C

8: triethylamine / N,N-dimethyl-formamide / 2 h / 50 °C

9: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

10: lithium hydroxide monohydrate; water / tetrahydrofuran / 1 h / 25 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; lithium hydroxide monohydrate; rhodium contaminated with carbon; water; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.8b00308

upstream raw materials:

1-deoxy-1-(methylamino)-D-glucitol

4-pentynoic acid

2,5-dichloroanisole

tert-butyl (4R)-4-[(4-cyclopropyl-1,2,3,4-tetrahydroquinoxalin-1-yl)carbonyl]-1,3-thiazolidine-3-carboxylate

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