2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester

Base Information

• Chemical Name: 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester
• CAS No.: 246506-78-5
• Molecular Formula: C₂₈H₃₆N₂O₆
• Molecular Weight: 496.604
• Mol file: 246506-78-5.mol

Synonyms:2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester

Chemical Property of 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester

There total 3 articles about 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid 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: 58.0%

L-Leucine benzyl ester (1738-69-8) + [1-benzyl-3-cyano-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-carbamic acid tert-butyl ester (246506-75-2) → 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester (246506-78-5)

Guidance literature:

[1-benzyl-3-cyano-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid tert-butyl ester; With ozone; In dichloromethane; at -78 ℃;

L-Leucine benzyl ester; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(99)01143-0

Reference yield:

Boc-D-Phe-OH (18942-49-9) → 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester (246506-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / EDCI / CH₂Cl₂ / 5 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

2.2: 58 percent / CH₂Cl₂ / -78 - 20 °C

With ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1016/S0040-4020(03)00860-3

Reference yield:

Boc-D-Phe-OH (18942-49-9) → 2-(3-tert-butoxycarbonylamino-2-oxo-4-phenylbutyrylamino)-4-methylpentanoic acid benzyl ester (246506-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / EDCI; DMAP

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 58 percent / CH₂Cl₂ / -78 °C

With dmap; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; 1.1: Condensation / 2.1: ozonolysis / 2.2: Substitution;

DOI:10.1016/S0040-4039(99)01143-0

upstream raw materials:

L-Leucine benzyl ester

[1-benzyl-3-cyano-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid tert-butyl ester

Boc-D-Phe-OH

Downstream raw materials:

1-{1-[2-(3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyrylamino)-4-methyl-pentanoyl]pyrrolidine-2-carbonyl}-pyrrolidine-2-carboxylic acid benzyl ester

(2S)-2-[[(2S,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid

(S-(R*,S*))-N-(3-amino-2-hydroxy-4-phenylbutyroyl)-L-leucine

bestatin

Refernces

• 1、 Wasserman, Harry H.,Xia, Mingde,Petersen, Anders K.,Jorgensen, Michael R.,Curtis, Erin A.. "Synthesis of the peptidic α-hydroxy amides phebestin, probestin, and bestatin from α-keto amide precursors". . p. 6163 - 6166. Retrieved 2007/10/03.