Bestatin Methyl Ester

Base Information

• Chemical Name: Bestatin Methyl Ester
• CAS No.: 65322-89-6
• Molecular Formula: C17H26N2O4
• Molecular Weight: 322.404
• DSSTox Substance ID: DTXSID20432965
• Nikkaji Number: J1.890.234F
• Wikidata: Q82247109
• Pharos Ligand ID: GNVNDHT7A59H
• ChEMBL ID: CHEMBL457092
• Mol file: 65322-89-6.mol

Synonyms:(-)-N-((2S,3R)-3-amino-2-hydroxy-4-phenyl-butyryl)-L-leucine methyl ester;bestatin methyl ester;ME-BS cpd

Chemical Property of Bestatin Methyl Ester

Chemical Property:

• Boiling Point: 535.1±50.0 °C(Predicted)
• PKA: 10.88±0.45(Predicted)
• PSA: 105.14000
• Density: 1.139±0.06 g/cm3(Predicted)
• LogP: 2.16180
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 322.18925731
• Heavy Atom Count: 23
• Complexity: 381

Purity/Quality:

98%Min ^*data from raw suppliers

BestatinMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)OC)NC(=O)C(C(CC1=CC=CC=C1)N)O
• Isomeric SMILES: CC(C)C[C@@H](C(=O)OC)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
• Uses: Bestatin Methyl Ester is an aminopeptidase inhibitor.

Technology Process of Bestatin Methyl Ester

There total 9 articles about Bestatin Methyl 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: 82.0%

[(3R)-tert-butoxycarbonylamino-(2S)-hydroxy-2,3-isopropylidene-4-phenylbutanoyl]-L-leucine methyl ester (685508-11-6) → methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate (65322-89-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 24h;

DOI:10.1021/jo0358269

Reference yield:

methanol (67-56-1) + bestatin (58970-76-6) → methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate (65322-89-6)

Guidance literature:

bestatin; With isopropyldimethylsilyl chloride; for 1h;

methanol; at 20 ℃;

Reference yield:

2-Phenylnitroethane (6125-24-2) → methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate (65322-89-6)

Guidance literature:

Multi-step reaction with 7 steps

1: activated Al₂O₃ / 24 h / -20 °C

2: H₂ / Raney-Ni / methanol / 16 h / 20 °C

3: 185 mg / aq. NaHCO₃ / ethyl acetate / 2 h / 20 °C

4: 87 percent / TsOH / toluene / 5 h / 50 °C

5: 89 percent / MeONa / methanol / 24 h / 20 °C

6: 95 percent / N-ethylmorpholine; isobutyl chloroformate / tetrahydrofuran / 1 h / -5 - 20 °C

7: 82 percent / TsOH / methanol / 24 h / 20 °C

With N-ethylmorpholine;; aluminum oxide; hydrogen; sodium methylate; sodium hydrogencarbonate; toluene-4-sulfonic acid; isobutyl chloroformate; nickel; In tetrahydrofuran; methanol; ethyl acetate; toluene;

DOI:10.1021/jo0358269

upstream raw materials:

[(3R)-tert-butoxycarbonylamino-(2S)-hydroxy-2,3-isopropylidene-4-phenylbutanoyl]-L-leucine methyl ester

(S)-Leu-OMe

2-Phenylnitroethane

(4R,5S)-4-benzyl-3-[(tert-butoxy)carbonyl]-2,2-dimethyl-1,3-oxazolidine-5-carboxylic acid

Downstream raw materials:

(S)-methyl 2-((2S,3R)-3-acetamido-4-(4-bromophenyl)-2-hydroxybutanamido)-4-methylpentanoate

(S)-methyl 2-((2S,3R)-3-acetamido-2-acetoxy-4-(4-bromophenyl)butanamido)-4-methylpentanoate

(S)-methyl 2-((2S,3R)-3-acetamido-2-hydroxy-4-phenylbutanamido)-4-methylpentanoate

(S)-methyl 2-((2S,3R)-3-acetamido-2-acetoxy-4-phenylbutanamido)-4-methylpentanoate