(2s,3s,5s)-5-[(N-Formyl-L-Leucyl)oxy]-2-Hexyl-3-Hydroxyhexadecanoic Acid

Base Information

• Chemical Name: (2s,3s,5s)-5-[(N-Formyl-L-Leucyl)oxy]-2-Hexyl-3-Hydroxyhexadecanoic Acid
• CAS No.: 130676-66-3
• Molecular Formula: C₂₉H₅₅NO₆
• Molecular Weight: 513.759
• UNII: LL6562DY22
• Wikidata: Q27459231
• Mol file: 130676-66-3.mol

Synonyms:130676-66-3;Orlistat (m1);(2s,3s,5s)-5-[(N-Formyl-L-Leucyl)oxy]-2-Hexyl-3-Hydroxyhexadecanoic Acid;Orlistat open ring (S,S)-isomer;LL6562DY22;Orlistat open ring (2S,3S,5S)-isomer;UNII-LL6562DY22;L-Leucine, N-formyl-, (1S)-1-((2S,3S)-3-carboxy-2-hydroxynonyl)dodecyl ester;L-Leucine, N-formyl-, (1S)-1-[(2S,3S)-3-carboxy-2-hydroxynonyl]dodecyl ester;(2S,3S,5S)-5-[(2S)-2-formamido-4-methylpentanoyl]oxy-2-hexyl-3-hydroxyhexadecanoic acid;DH9;SCHEMBL3358240;(2S,3S,5S)-5-[(N-Formyl-L-leucyl)oxy]-2-hexyl-3-hydroxyhexadecanoic Acid(Orlistat Impurity);Q27459231;(2S,3S,5S)-5-((Formyl-L-leucyl)oxy)-2-hexyl-3-hydroxyhexadecanoic acid;(2S,3S,5S)-5-[(N-Formyl-L-leucyl)oxy]-2-hexyl-3-hydroxyhexadecanoic Acid (Orlistat Impurity) (>80%);(2S,3S,5S)-5-[(N-Formyl-L-leucyl)oxy]-2-hexyl-3-hydroxyhexadecanoic Acid (Orlistat Impurity) (>80%)

Chemical Property of (2s,3s,5s)-5-[(N-Formyl-L-Leucyl)oxy]-2-Hexyl-3-Hydroxyhexadecanoic Acid

Chemical Property:

• Refractive Index: 1.479
• Boiling Point: 645.8±55.0 °C(Predicted)
• PKA: 4.37±0.50(Predicted)
• PSA: 112.93000
• Density: 1.005±0.06 g/cm3(Predicted)
• LogP: 7.42880
• Storage Temp.: -86°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 25
• Exact Mass: 513.40293847
• Heavy Atom Count: 36
• Complexity: 568

Purity/Quality:

99% ^*data from raw suppliers

(2S,3S,5S)-5-[(N-Formyl-L-leucyl)oxy]-2-hexyl-3-hydroxyhexadecanoicAcid(OrlistatImpurity)(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(C(CCCCCC)C(=O)O)O)OC(=O)C(CC(C)C)NC=O
• Isomeric SMILES: CCCCCCCCCCC[C@@H](C[C@@H]([C@H](CCCCCC)C(=O)O)O)OC(=O)[C@H](CC(C)C)NC=O
• Uses: A degradation product of Tetrahydrolipstatin (Orlistat). Orlistat impurity A product from thermal and hydrolytic degradation of Orlistat. Orlistat impurity A metabolite of Orlistat (O686500).

Technology Process of (2s,3s,5s)-5-[(N-Formyl-L-Leucyl)oxy]-2-Hexyl-3-Hydroxyhexadecanoic Acid

There total 4 articles about (2s,3s,5s)-5-[(N-Formyl-L-Leucyl)oxy]-2-Hexyl-3-Hydroxyhexadecanoic 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: 21.0%

N-Formyl-L-leucine (S)-1-<(2S,3S)-2-(Benzyloxy)-3-<(benzyloxy)carbonyl>-3-hexylpropyl>dodecyl Ester (130705-32-7) → (2S,3S,5S)-5-<<(S)-2-(Formylamino)-4-methylpentanoyl>oxy>-2-hexyl-3-hydroxyhexadecanoic Acid (130676-66-3,130793-28-1) + N-Formyl-L-leucine (3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester (130676-65-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1002/hlca.19900730427

Reference yield:

Tetrahydrolipstatin (96829-58-2,104872-04-0,104872-27-7,104872-28-8,111466-61-6,111466-62-7,111466-63-8,130193-40-7,130193-41-8,130193-42-9,130193-43-0,1225451-00-2) → N-Formyl-L-leucine (S,E)-1-(Non-2-enyl)dodecyl Ester (130676-63-0) + (2S,3S,5S)-5-<<(S)-2-(Formylamino)-4-methylpentanoyl>oxy>-2-hexyl-3-hydroxyhexadecanoic Acid (130676-66-3,130793-28-1) + (S)-3-Hexyl-5,6-dihydro-6-undecyl-2H-pyran-2-one (130676-64-1) + (3S,4R,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one (130793-26-9) + N-Formyl-L-leucine (3S,4R,6S)-3-Hexyl-3,4,5,6-tetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester (130793-27-0) + N-Formyl-L-leucine (3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester (130676-65-2)

Guidance literature:

at 45 - 85 ℃; Product distribution; hydrolytic degradation on storage (a: 85percent rel. humidity; b: dry); time: 3 d to 6 months; degradation pathways; degradation in presence of OCHPheOH;

DOI:10.1002/hlca.19900730427

Reference yield:

N-formyl-L-leucine (5338-45-4,44978-39-4,89921-44-8,6113-61-7) → (2S,3S,5S)-5-<<(S)-2-(Formylamino)-4-methylpentanoyl>oxy>-2-hexyl-3-hydroxyhexadecanoic Acid (130676-66-3,130793-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / N,N'-dicyclohexylcarbodiimide

2: 19 percent / hydrogen / 5percent Pd/C / tetrahydrofuran / 2 h / Ambient temperature

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1002/hlca.19900730427

upstream raw materials:

N-Formyl-L-leucine (S)-1-<(2S,3S)-2-(Benzyloxy)-3-<(benzyloxy)carbonyl>-3-hexylpropyl>dodecyl Ester

Tetrahydrolipstatin

N-formyl-L-leucine

benzyl (2S,3S,5R)-3-(benzyloxy)-2-hexyl-5-hydroxyhexadecanoate

Refernces