[(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide

Base Information

• Chemical Name: [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide
• CAS No.: 1027137-63-8
• Molecular Formula: C₂₈H₄₇N₃O₅
• Molecular Weight: 505.698
• Mol file: 1027137-63-8.mol

Synonyms:[(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide

Chemical Property of [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide

There total 17 articles about [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl 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:

N-tert-butoxycarbonyl-L-leucine methyl ester (63096-02-6) → [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide (1027137-63-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: diisobutylaluminium hydride / toluene / 0.17 h / -78 - 0 °C

2.1: lithium diisopropylamide / tetrahydrofuran / 0.33 h / -78 °C

2.2: 29 percent / tetrahydrofuran / 0.67 h / -78 °C

3.1: 91 percent / phosphorous oxychloride / CH₂Cl₂ / 15 h

4.1: 91 percent / diisobutylaluminium hydride / tetrahydrofuran / 0.75 h / 0 °C

5.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

6.1: 588 mg / dimethylsulfoxide / 20 h / 50 °C

7.1: NaOH; H₂O₂ / ethanol; H₂O / 0 °C

8.1: acetic acid / H₂O / 72 h / 20 °C

9.1: 211 mg / benzene / 1 h / Heating

10.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

10.2: 69 percent / tetrahydrofuran / 0.58 h / -78 °C

11.1: LiOH / tetrahydrofuran; H₂O / 20 °C

12.1: 1.250 g / imidazole / dimethylformamide / 24 h / 20 °C

13.1: 89 percent / 1-hydroxybenzotriazole; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine / dimethylformamide; CH₂Cl₂ / 36 h / 20 °C

14.1: 76 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

15.1: CF₃COOH / CH₂Cl₂ / 0.5 h / 20 °C

16.1: 245 mg / 1-hydroxybenzotriazole; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine / dimethylformamide / 24 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; sodium hydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1080/00397910600977509

Reference yield:

tert-butoxycarbonyl-L-leucinal (58521-45-2) → [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide (1027137-63-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 0.33 h / -78 °C

1.2: 29 percent / tetrahydrofuran / 0.67 h / -78 °C

2.1: 91 percent / phosphorous oxychloride / CH₂Cl₂ / 15 h

3.1: 91 percent / diisobutylaluminium hydride / tetrahydrofuran / 0.75 h / 0 °C

4.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

5.1: 588 mg / dimethylsulfoxide / 20 h / 50 °C

6.1: NaOH; H₂O₂ / ethanol; H₂O / 0 °C

7.1: acetic acid / H₂O / 72 h / 20 °C

8.1: 211 mg / benzene / 1 h / Heating

9.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

9.2: 69 percent / tetrahydrofuran / 0.58 h / -78 °C

10.1: LiOH / tetrahydrofuran; H₂O / 20 °C

11.1: 1.250 g / imidazole / dimethylformamide / 24 h / 20 °C

12.1: 89 percent / 1-hydroxybenzotriazole; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine / dimethylformamide; CH₂Cl₂ / 36 h / 20 °C

13.1: 76 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

14.1: CF₃COOH / CH₂Cl₂ / 0.5 h / 20 °C

15.1: 245 mg / 1-hydroxybenzotriazole; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine / dimethylformamide / 24 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; sodium hydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1080/00397910600977509

Reference yield:

(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester (82010-31-9) → [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide (1027137-63-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: TEA; pyridine*SO₃ / CH₂Cl₂; dimethylsulfoxide / 0.58 h / cooling

2.1: lithium diisopropylamide / tetrahydrofuran / 0.33 h / -78 °C

2.2: 29 percent / tetrahydrofuran / 0.67 h / -78 °C

3.1: 91 percent / phosphorous oxychloride / CH₂Cl₂ / 15 h

4.1: 91 percent / diisobutylaluminium hydride / tetrahydrofuran / 0.75 h / 0 °C

5.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

6.1: 588 mg / dimethylsulfoxide / 20 h / 50 °C

7.1: NaOH; H₂O₂ / ethanol; H₂O / 0 °C

8.1: acetic acid / H₂O / 72 h / 20 °C

9.1: 211 mg / benzene / 1 h / Heating

10.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

10.2: 69 percent / tetrahydrofuran / 0.58 h / -78 °C

11.1: LiOH / tetrahydrofuran; H₂O / 20 °C

12.1: 1.250 g / imidazole / dimethylformamide / 24 h / 20 °C

13.1: 89 percent / 1-hydroxybenzotriazole; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine / dimethylformamide; CH₂Cl₂ / 36 h / 20 °C

14.1: 76 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 20 °C

15.1: CF₃COOH / CH₂Cl₂ / 0.5 h / 20 °C

16.1: 245 mg / 1-hydroxybenzotriazole; N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride; N-methylmorpholine / dimethylformamide / 24 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; sodium hydroxide; TEA; tetrabutyl ammonium fluoride; dihydrogen peroxide; sulfur trioxide pyridine complex; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1080/00397910600977509

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(4S,5S)-N-Boc-5-(carbethoxymethyl)-2,2-dimethyl-4-(2-methylpropyl)-1,3-oxazolidine

[(2R,4S,5S)-5-(N-Boc-amino)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide

[(2R,4S,5S)-5-(N-Boc-amino)-4-[(tert-butyldimethylsilyl)oxy]-2,7-dimethyloctanoyl] N'-isobutyl amide

Downstream raw materials:

C₃₁H₄₃N₃O₆

C₃₃H₅₆N₄O₆

C₃₄H₅₈N₄O₆

C₃₄H₅₈N₄O₆