N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester

Base Information

• Chemical Name: N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester
• CAS No.: 121445-53-2
• Molecular Formula: C₂₃H₂₈N₄O₄
• Molecular Weight: 424.5
• Mol file: 121445-53-2.mol

Synonyms:N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester

Chemical Property of N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester

There total 12 articles about N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester 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: 68.0%

L-leucine benzyl ester p-toluenesulfonate (1738-77-8) + (2S,3R)-3-azido-2-hydroxy-4-phenylbutanoic acid (121445-52-1) → N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester (121445-53-2)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 12h;

DOI:10.1021/jo00278a050

Reference yield:

phenylmagnesium bromide (100-58-3) → N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester (121445-53-2)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / 1) 5 deg C, 1 h, 2) room temperature, 1.5 h

2: 7.7 g / NaIO₄ / diethyl ether; H₂O / 2 h / Ambient temperature

3: 53 percent / Jones reagent / acetone / 0.25 h / 0 °C

4: 91.7 percent / H₂ / Pd-C / methanol

5: 82.7 percent / 1-ethyl-3-(3-dimethylaminoproyl)carbodiimide hydrochloride / CH₂Cl₂ / 2 h

6: 43 percent / CF₃COOH / H₂O / 0.5 h / 0 °C

7: 1) 2-fluoro-1-methylpyridinium p-toluenesulfonate, 2) NaN₃ / 1) CHCl₃, room tempetarure, 1h, 2) HMPA, 80 deg C, 2 h

With sodium periodate; sodium azide; jones reagent; hydrogen; 1-methyl-2-fluoropyridinium p-toluenesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1271/bbb.60.534

Reference yield:

(3aS,6S,6aS)-2,2-dimethyl-6-phenyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (176895-32-2) → N-<(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl>-L-leucine benzyl ester (121445-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 91.7 percent / H₂ / Pd-C / methanol

2: 82.7 percent / 1-ethyl-3-(3-dimethylaminoproyl)carbodiimide hydrochloride / CH₂Cl₂ / 2 h

3: 43 percent / CF₃COOH / H₂O / 0.5 h / 0 °C

4: 1) 2-fluoro-1-methylpyridinium p-toluenesulfonate, 2) NaN₃ / 1) CHCl₃, room tempetarure, 1h, 2) HMPA, 80 deg C, 2 h

With sodium azide; hydrogen; 1-methyl-2-fluoropyridinium p-toluenesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; water;

DOI:10.1271/bbb.60.534

upstream raw materials:

L-leucine benzyl ester p-toluenesulfonate

(2S,3R)-3-azido-2-hydroxy-4-phenylbutanoic acid

(S)-2-((2S,3S)-2,3-Dihydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid benzyl ester

phenylmagnesium bromide

Downstream raw materials:

bestatin

Refernces

• 1、 Pearson,Hines. "Synthesis of β-amino-α-hydroxy acids via aldol condensation of a chiral glycolate enolate. Synthesis of (-)-bestatin". . p. 4235 - 4237. Retrieved 2007/10/02.