Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-tetrahydro-3-hexyl-2-oxo-6-undecyl-2H-pyran-4-yl ester)

Base Information

• Chemical Name: Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-tetrahydro-3-hexyl-2-oxo-6-undecyl-2H-pyran-4-yl ester)
• CAS No.: 130793-27-0
• Molecular Formula: C₂₉H₅₃NO₅
• Molecular Weight: 495.744
• Hs Code.: 2932206000
• Mol file: 130793-27-0.mol

Synonyms:Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-tetrahydro-3-hexyl-2-oxo-6-undecyl-2H-pyran-4-yl ester);3S-(3α,4β,6β)]-N-ForMyl-L-leucine 3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester;N-ForMyl-L-leucine (3S,4R,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl Ester;Orlistat USP RC D;Orlistat Related CoMpound D;N-Formyl-L-leucine (3S,4R,6S)-3-hexyl-2-oxo-6-undecyltetrahydro-2H-pyran-4-yl ester;Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-3-hexyl-2-oxo-6-undecyltetrahydro-2H-pyran-4-yl ester)

Chemical Property of Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-tetrahydro-3-hexyl-2-oxo-6-undecyl-2H-pyran-4-yl ester)

Chemical Property:

• Boiling Point: 632.6±50.0 °C(Predicted)
• PKA: 14.53±0.23(Predicted)
• PSA: 81.70000
• Density: 0.99±0.1 g/cm3(Predicted)
• LogP: 7.90870
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

N-Formyl-L-leucine(3S,4R,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,4R,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl ester is an impurity of Orlistat (O686500). Orlistat USP Related Compound D. N-Formyl-L-leucine (3S,4R,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl ester is an impurity of Orlistat (O686500).

Technology Process of Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-tetrahydro-3-hexyl-2-oxo-6-undecyl-2H-pyran-4-yl ester)

There total 6 articles about Orlistat Related Compound D (10 mg) (N-formyl-L-leucine (3S,4R,6S)-tetrahydro-3-hexyl-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: 14.0%

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) → (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)

Guidance literature:

With phosphate buffer; In 1,4-dioxane; for 120h; Further byproducts given; Heating;

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:

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) → 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)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Et₃N, AcOH, 2.) (i-Pr)2EtN, 4-(dimethylamino)pyridine / 1.) 50 deg C, 4 d, 2.) pentane, Et₂O, r.t.

2: 27 percent / (Bu₄N)NO₃ / toluene / 13 h / Heating

3: 69 percent / hydrogen / 10 percent Pd/C / propan-2-ol / 2 h / 7500.6 Torr / Ambient temperature

4: TsOH / acetonitrile / 2 h / Ambient temperature

With dmap; hydrogen; tetrabutylammonium nitrate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In isopropyl alcohol; toluene; acetonitrile;

DOI:10.1002/hlca.19920750513

upstream raw materials:

Tetrahydrolipstatin

Methyl (2S,3R,5S)-5-<(S)-2-formamido-4-methylpentanoyloxy>-2-hexyl-3-hydroxyhexadecanoate

Orlistat

Methyl (2S,3R,5S)-5-<(S)-2-formamido-4-methylpentanoyloxy>-2-hexyl-3-(nitryloxy)hexadecanoate

Refernces

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