(2S)-3-hydroxy-2-[[2-[[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]amino]acetyl]amino]propanoic acid

Base Information

• Chemical Name: (2S)-3-hydroxy-2-[[2-[[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]amino]acetyl]amino]propanoic acid
• CAS No.: 96095-04-4
• Molecular Formula: C₃₇H₇₀N₂O₇
• Molecular Weight: 654.972
• DSSTox Substance ID: DTXSID30914666
• Nikkaji Number: J979.763G
• Wikidata: Q77564600
• Metabolomics Workbench ID: 103906
• Mol file: 96095-04-4.mol

Synonyms:WB 3559 D;WB-3559D

Chemical Property of (2S)-3-hydroxy-2-[[2-[[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]amino]acetyl]amino]propanoic acid

Chemical Property:

• Vapor Pressure: 1.32E-29mmHg at 25°C
• Boiling Point: 800°Cat760mmHg
• Flash Point: 437.6°C
• Density: 1.01g/cm³
• XLogP3: 11.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 33
• Exact Mass: 654.51830258
• Heavy Atom Count: 46
• Complexity: 788

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CCCCCCCCCCCC(CC(=O)NCC(=O)NC(CO)C(=O)O)OC(=O)CCCCCCCCCCCC(C)C
• Isomeric SMILES: CC(C)CCCCCCCCCCC[C@H](CC(=O)NCC(=O)N[C@@H](CO)C(=O)O)OC(=O)CCCCCCCCCCCC(C)C

Technology Process of (2S)-3-hydroxy-2-[[2-[[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]amino]acetyl]amino]propanoic acid

There total 81 articles about (2S)-3-hydroxy-2-[[2-[[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]amino]acetyl]amino]propanoic acid 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: 74.0%

(R)-1-((2-(((S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)amino)-2-oxoethyl)amino)-15-methyl-1-oxohexadecan-3-yl 13-methyltetradecanoate (103196-65-2) → (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine (179095-19-3,96095-04-4)

Guidance literature:

With potassium trimethylsilonate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tet.2016.10.010

Reference yield: 70.0%

N-{N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl}-L-serine benzyl ester (214406-45-8) → (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine (179095-19-3,96095-04-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)83044-5

Reference yield:

13-methyltetradecanoic acid (2485-71-4) → (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine (179095-19-3,96095-04-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / DCC, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

2: 90 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / Ambient temperature

3: oxalyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

5: 98 percent / H₂ / Pd/C / ethyl acetate / 2 h / Ambient temperature

6: 72 percent / DCC / CH₂Cl₂ / 2 h / Ambient temperature

7: 70 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / Ambient temperature

With dmap; oxalyl dichloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(98)83044-5

upstream raw materials:

L-serin

N-{N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl}-L-serine benzyl ester

13-methyltetradecanoic acid

(3R)-ethyl-3-hydroxy-15-methylhexadecanoate