6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide

Base Information

• Chemical Name: 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide
• CAS No.: 906663-04-5
• Molecular Formula: C₃₁H₄₅N₃O₄S₂
• Molecular Weight: 587.848
• Mol file: 906663-04-5.mol

Synonyms:6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide

Chemical Property of 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide

There total 13 articles about 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide 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:

4-(3-methoxycarbonyl-propynoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (911285-53-5) → 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide (906663-04-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 96 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 3 h / 2585.74 Torr

2.1: 85 percent / NaBH₄ / methanol / 5 h / -15 - 0 °C

3.1: 95 percent / AcOH / toluene / 5 h / Heating

4.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 70 percent / tetrahydrofuran / 0.67 h / -78 °C

5.1: 75 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

6.1: 66 percent / imidazole; 1,1'-(azodicarbonyl)dipiperidine; PMe₃ / CH₂Cl₂; toluene / 24 h / 20 °C

7.1: Me₃Al / toluene; CH₂Cl₂ / 0.25 h

7.2: 88 percent / CH₂Cl₂; toluene / 45 °C

8.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 88 mg / PyBOP; iPr₂NEt / CH₂Cl₂ / 3 h / 0 - 20 °C

10.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

11.1: 120 mg / PyBOP; iPr₂NEt / CH₂Cl₂ / 3 h / 0 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; trimethylaluminum; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jm060154a

Reference yield:

(4S,1'S)-4-(1-hydroxy-3-methoxycarbonylprop-2-ynyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (906662-73-5) → 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide (906663-04-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: H₂ / Pd/BaSO₄ / ethyl acetate / 3 h / 2585.74 Torr

2.1: 95 percent / AcOH / toluene / 5 h / Heating

3.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 70 percent / tetrahydrofuran / 0.67 h / -78 °C

4.1: 75 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

5.1: 66 percent / imidazole; 1,1'-(azodicarbonyl)dipiperidine; PMe₃ / CH₂Cl₂; toluene / 24 h / 20 °C

6.1: Me₃Al / toluene; CH₂Cl₂ / 0.25 h

6.2: 88 percent / CH₂Cl₂; toluene / 45 °C

7.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 88 mg / PyBOP; iPr₂NEt / CH₂Cl₂ / 3 h / 0 - 20 °C

9.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

10.1: 120 mg / PyBOP; iPr₂NEt / CH₂Cl₂ / 3 h / 0 - 20 °C

With 1H-imidazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; trimethylaluminum; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; Pd-BaSO₄; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jm060154a

Reference yield:

(4S,1'R)-4-(1-hydroxy-3-methoxycarbonylprop-2-ynyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (906662-74-6) → 6-benzylsulfanyl-5-[2-(3-benzylsulfanylpropionylamino)propionylamino]-4-hydroxy-2-methylhexanoic acid butylamide (906663-04-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 75 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: 96 percent / H₂ / Pd/BaSO₄ / ethyl acetate / 3 h / 2585.74 Torr

3.1: 85 percent / NaBH₄ / methanol / 5 h / -15 - 0 °C

4.1: 95 percent / AcOH / toluene / 5 h / Heating

5.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: 70 percent / tetrahydrofuran / 0.67 h / -78 °C

6.1: 75 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 48 h / 20 °C

7.1: 66 percent / imidazole; 1,1'-(azodicarbonyl)dipiperidine; PMe₃ / CH₂Cl₂; toluene / 24 h / 20 °C

8.1: Me₃Al / toluene; CH₂Cl₂ / 0.25 h

8.2: 88 percent / CH₂Cl₂; toluene / 45 °C

9.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

10.1: 88 mg / PyBOP; iPr₂NEt / CH₂Cl₂ / 3 h / 0 - 20 °C

11.1: TFA / CH₂Cl₂ / 0.5 h / 20 °C

12.1: 120 mg / PyBOP; iPr₂NEt / CH₂Cl₂ / 3 h / 0 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; trimethylaluminum; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1021/jm060154a

upstream raw materials:

5-(2-aminopropionylamino)-6-benzylsulfanyl-4-hydroxy-2-methylhexanoic acid butylamide

3-(benzylthio)propanoic acid

(1S,2'S,4'R)-[2-hydroxy-1-(4-methyl-5-oxotetrahydrofuran-2-yl)ethyl]carbamic acid tert-butyl ester

(4S,2'S)-2,2-dimethyl-4-(5-oxotetrahydrofuran-2-yl)oxazolidine-3-carboxylic acid tert-butyl ester

Refernces