[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate

Base Information

• Chemical Name: [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate
• CAS No.: 96829-59-3
• Molecular Formula: C29H49NO5
• Molecular Weight: 491.712
• European Community (EC) Number: 619-246-0
• Wikipedia: Lipstatin
• Mol file: 96829-59-3.mol

Synonyms:lipstatin

Chemical Property of [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.485
• Boiling Point: 627.402 °C at 760 mmHg
• PKA: 14.57±0.23(Predicted)
• Flash Point: 333.241 °C
• PSA: 81.70000
• Density: 0.994 g/cm³
• LogP: 7.46070
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 8.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 21
• Exact Mass: 491.36107366
• Heavy Atom Count: 35
• Complexity: 658

Purity/Quality:

98%min ^*data from raw suppliers

Lipstatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1C(OC1=O)CC(CC=CCC=CCCCCC)OC(=O)C(CC(C)C)NC=O
• Isomeric SMILES: CCCCCC[C@H]1[C@@H](OC1=O)C[C@H](CC=CCC=CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
• Uses: Lipstatin, a potent inhibitor of the pancreas lipase, is reported to be useful in the treatment and/or prevention of obesity and related diseases. Lipstatin is a potent irreversible inhibitor of pancreatic lipase, produced by Streptomyces toxytricini and first reported in 1987. In vivo, lipstatin acts to block the absorption of triglycerides while allowing fatty acid absorption. The tetrahydro analogue of lipstatin, orlistat, although less potent, was developed for the treatment of obesity.

Technology Process of [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate

There total 11 articles about [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate 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: 50.0%

N-formyl-L-leucine (5338-45-4,44978-39-4,89921-44-8,6113-61-7) + 4-<(4Z,7Z)-2-hydroxytrideca-4,7-dienyl>-3-hexyloxetan-2-one (108102-73-4) → (-)-lipstatin (96829-59-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 1.5h; 0 deg C to RT;

DOI:10.1039/P19930001549

Reference yield:

(Z)-non-3-en-1-ol (10340-23-5) → (-)-lipstatin (96829-59-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / PPh₃Br₂, pyridine / acetonitrile / 1 h / -7 to RT

2: 100 percent / acetonitrile / 48 h / Heating

3: 86 percent / NaN(SiMe₃)2 / tetrahydrofuran / 12 h / -100 deg C to RT

4: 93 percent / DIBAH / CH₂Cl₂ / 1 h / -90 °C

5: 81 percent / EtAlCl₂ / diethyl ether; hexane / 2.5 h / -40 to -20 deg C

6: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT

7: 70 percent / Bu₄NF / tetrahydrofuran / 0.25 h / -90 °C

8: 50 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT

With pyridine; hydrogen fluoride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; ethylaluminum dichloride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; dibromotriphenylphosphorane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1039/P19930001549

Reference yield:

(Z)-3-nonenal (31823-43-5) → (-)-lipstatin (96829-59-3)

Guidance literature:

Multi-step reaction with 9 steps

1: LiAlH₄ / tetrahydrofuran / 2.5 h / -90 to -20 deg C

2: 90 percent / PPh₃Br₂, pyridine / acetonitrile / 1 h / -7 to RT

3: 100 percent / acetonitrile / 48 h / Heating

4: 86 percent / NaN(SiMe₃)2 / tetrahydrofuran / 12 h / -100 deg C to RT

5: 93 percent / DIBAH / CH₂Cl₂ / 1 h / -90 °C

6: 81 percent / EtAlCl₂ / diethyl ether; hexane / 2.5 h / -40 to -20 deg C

7: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT

8: 70 percent / Bu₄NF / tetrahydrofuran / 0.25 h / -90 °C

9: 50 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT

With pyridine; lithium aluminium tetrahydride; hydrogen fluoride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; ethylaluminum dichloride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; dibromotriphenylphosphorane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1039/P19930001549

upstream raw materials:

N-formyl-L-leucine

4-<(4Z,7Z)-2-hydroxytrideca-4,7-dienyl>-3-hexyloxetan-2-one

(Z)-non-3-en-1-ol

(Z)-3-nonenal

Downstream raw materials:

Orlistat

orlistat

Refernces