(2R,3S,4S)-N-(2-(Benzylamino)-4-((N-((benzyloxy)carbonyl)-L-alanyl)amino)-3-hydroxy-5-phenylpentanoyl)-L-valine benzylamide

Base Information

• Chemical Name: (2R,3S,4S)-N-(2-(Benzylamino)-4-((N-((benzyloxy)carbonyl)-L-alanyl)amino)-3-hydroxy-5-phenylpentanoyl)-L-valine benzylamide
• CAS No.: 161594-18-9
• Molecular Formula: C₄₁H₄₉N₅O₆
• Molecular Weight: 707.87
• DSSTox Substance ID: DTXSID60167204
• Wikidata: Q83036529
• ChEMBL ID: CHEMBL102328
• Mol file: 161594-18-9.mol

Synonyms:161594-18-9;(2R,3S,4S)-N-(2-(Benzylamino)-4-((N-((benzyloxy)carbonyl)-L-alanyl)amino)-3-hydroxy-5-phenylpentanoyl)-L-valine benzylamide;Statine deriv. 19;BDBM939;CHEMBL102328;DTXSID60167204;Ala-Val-Sta, 5PhBuCOOH deriv.;(2R,3S,4S)-N-[2-(Benzylamino)-4-[[N-[(benzyloxy)carbonyl]-L-alanyl]amino]-3-hydroxy-5- phenylpentanoyl]-L-valine benzylamide;benzyl N-[(1S)-1-{[(2S,3R,4R)-4-(benzylamino)-4-{[(1S)-1-(benzylcarbamoyl)-2-methylpropyl]carbamoyl}-3-hydroxy-1-phenylbutan-2-yl]carbamoyl}ethyl]carbamate;benzyl N-[(1S)-2-[[(1S,2R,3R)-1-benzyl-3-(benzylamino)-4-[[(1S)-1-(benzylcarbamoyl)-2-methyl-propyl]amino]-2-hydroxy-4-oxo-butyl]amino]-1-methyl-2-oxo-ethyl]carbamate

Chemical Property of (2R,3S,4S)-N-(2-(Benzylamino)-4-((N-((benzyloxy)carbonyl)-L-alanyl)amino)-3-hydroxy-5-phenylpentanoyl)-L-valine benzylamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 989.3°Cat760mmHg
• Flash Point: 552.1°C
• Density: 1.198g/cm³
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 19
• Exact Mass: 707.36828430
• Heavy Atom Count: 52
• Complexity: 1080

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NCC1=CC=CC=C1)NC(=O)C(C(C(CC2=CC=CC=C2)NC(=O)C(C)NC(=O)OCC3=CC=CC=C3)O)NCC4=CC=CC=C4
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H]([C@H](C(=O)N[C@@H](C(C)C)C(=O)NCC2=CC=CC=C2)NCC3=CC=CC=C3)O)NC(=O)OCC4=CC=CC=C4

Technology Process of (2R,3S,4S)-N-(2-(Benzylamino)-4-((N-((benzyloxy)carbonyl)-L-alanyl)amino)-3-hydroxy-5-phenylpentanoyl)-L-valine benzylamide

There total 9 articles about (2R,3S,4S)-N-(2-(Benzylamino)-4-((N-((benzyloxy)carbonyl)-L-alanyl)amino)-3-hydroxy-5-phenylpentanoyl)-L-valine benzylamide 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:

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (124818-94-6,116246-06-1) → SDZ 282392 (161594-18-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 120 h / Ambient temperature

2: 83 percent / ethanol / 48 h / 60 °C

3: 92 percent / 1N aq. NaOH / tetrahydrofuran / 10 h / Ambient temperature

4: 63 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / dimethylformamide / 24 h / Ambient temperature

5: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: dioxane / Ambient temperature

With sodium hydroxide; benzotriazol-1-ol; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00045a013

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → SDZ 282392 (161594-18-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / toluene / 1 h / 80 °C

2: 62 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 120 h / Ambient temperature

3: 83 percent / ethanol / 48 h / 60 °C

4: 92 percent / 1N aq. NaOH / tetrahydrofuran / 10 h / Ambient temperature

5: 63 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / dimethylformamide / 24 h / Ambient temperature

6: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

7: dioxane / Ambient temperature

With sodium hydroxide; benzotriazol-1-ol; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00045a013

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → SDZ 282392 (161594-18-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 6.32 g / (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / -55 °C

2: 80 percent / toluene / 1 h / 80 °C

3: 62 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 120 h / Ambient temperature

4: 83 percent / ethanol / 48 h / 60 °C

5: 92 percent / 1N aq. NaOH / tetrahydrofuran / 10 h / Ambient temperature

6: 63 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / dimethylformamide / 24 h / Ambient temperature

7: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

8: dioxane / Ambient temperature

With sodium hydroxide; oxalyl dichloride; benzotriazol-1-ol; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00045a013

upstream raw materials:

(2R,3S,4S)-N-(4-amino-2-(benzylamino)-3-hydroxy-5-phenylpentanoyl)valine benzamide

(N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

Boc-L-phenylalaninal