benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

Base Information

• Chemical Name: benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate
• CAS No.: 60016-66-2
• Molecular Formula: C₃₁H₃₆N₂O₆
• Molecular Weight: 532.637
• Mol file: 60016-66-2.mol

Synonyms:benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

Chemical Property of benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

There total 21 articles about benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate 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: 96.0%

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-tert-butyldimethylsiloxy-4-phenyl-butanoyl]-L-leucinate (318499-01-3) → benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate (60016-66-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1021/ol006816m

Reference yield: 95.0%

L-leucine benzyl ester p-toluenesulfonate (1738-77-8) + (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid (59969-65-2,76498-22-1) → benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate (60016-66-2)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)91124-4

Reference yield:

(4S,5R)-4-methoxycarbonylmethyl-5-phenyloxazolidin-2-one (178897-35-3) → benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate (60016-66-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83 percent / Ag₂CO₃ / toluene / 6 h / 60 °C

2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: 1.95 g / 3-phenyl-2-(phenylsulfonyl)oxaziridine / tetrahydrofuran / 1 h / -78 °C

3.1: 86 percent / H₂; HCl / Pd/C / H₂O; dioxane / 4 h / 25 °C / 2574.28 Torr

4.1: 85 percent / NaHCO₃ / H₂O; ethyl acetate / 17 h / 25 °C

5.1: 60 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / -20 - 25 °C

6.1: aq. NH₃ / 1 h / 25 °C

6.2: 187 mg / aq. NaOH / dioxane / 1 h / 25 °C

7.1: 161 mg / DCC; 1-hydroxybenzotriazole; Et₃N / CH₂Cl₂; tetrahydrofuran / 17 h / 25 °C

With hydrogenchloride; ammonium hydroxide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; silver carbonate; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; toluene; 1.1: Alkylation / 2.1: Metallation / 2.2: Oxidation / 3.1: Hydrogenolysis / 4.1: Condensation / 5.1: Esterification / 6.1: ammonolysis / 6.2: Hydrolysis / 7.1: Condensation;

DOI:10.1271/bbb.63.1304

upstream raw materials:

L-Leucine benzyl ester

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid

L-leucine benzyl ester p-toluenesulfonate

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-tert-butyldimethylsiloxy-4-phenyl-butanoyl]-L-leucinate

Downstream raw materials:

nitrobestatin

Bestatin hydrochloride

bestatin

Refernces

• 1、 Seki, Masahiko,Nakao, Kazuya. "Novel synthesis of (-)-bestatin from L-aspartic acid". . p. 1304 - 1307. Retrieved 2007/10/03.