N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester

Base Information

• Chemical Name: N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester
• CAS No.: 130676-65-2
• Molecular Formula: C₂₉H₅₃NO₅
• Molecular Weight: 495.744
• Mol file: 130676-65-2.mol

Synonyms:L-Leucine,N-formyl-, 3-hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl ester, [3S-(3a,4a,6b)]-; Ro 40-4441

Chemical Property of N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >90°C
• Boiling Point: 632.638°C at 760 mmHg
• Flash Point: 336.408°C
• PSA: 81.70000
• Density: 1.002g/cm³
• LogP: 7.90870
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

N-Formyl-L-leucine(3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-ylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl ester is an impurity of Orlistat (O686500). N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester is a by-product during the synthesis of N-Formyl-L-leucine (3S,4R,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester (F700570). An impurity of Orlistat (O686500). Orlistat USP Related Compound D. An deuterated analog of an impurity in the synthesis of Orlistat.

Technology Process of N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester

There total 7 articles about N-Formyl-L-leucine (3S,4S,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl 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: 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + Orlistat (104872-04-0,104872-27-7,104872-28-8,111466-61-6,111466-62-7,111466-63-8,130193-40-7,130193-41-8,130193-42-9,130193-43-0,96829-58-2,1225451-00-2) → (S)-3-Hexyl-5,6-dihydro-6-undecyl-2H-pyran-2-one (130676-64-1) + (3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one (68711-33-1) + 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) + Methyl (2S,3S,5S)-2-hexyl-3,5-dihydroxyhexadecanoate (145643-78-3) + Methyl (2S,3S,5S)-3-<(S)-2-formamido-4-methylpentanoyloxy>-2-hexyl-5-hydroxyhexadecanoate (145643-72-7,145682-66-2) + Methyl (2S,3S,5S)-5-<(S)-2-formamido-4-methylpentanoyloxy>-2-hexyl-3-hydroxyhexadecanoate (145643-71-6,145682-68-4)

Guidance literature:

Product distribution; Mechanism; 1.) human carboxyl-ester lipase, aq. buffer pH 7.0, 37 deg C, 2.) Et₂O;

DOI:10.1002/hlca.19920750513

upstream raw materials:

diazomethane

Orlistat

N-formyl-L-leucine

(3S,4S,6S)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

Refernces

• 1、 Stalder,Schneider,Oesterhelt. "Tetrahydrolipstatin: Thermal and hydrolytic degradation". . p. 1022 - 1036. Retrieved 2007/10/02.