Product Name

  • Name

    Lipstatin

  • EINECS 619-246-0
  • CAS No. 96829-59-3
  • Article Data1
  • CAS DataBase
  • Density 0.994 g/cm3
  • Solubility
  • Melting Point
  • Formula C29H49NO5
  • Boiling Point 627.402 °C at 760 mmHg
  • Molecular Weight 491.712
  • Flash Point 333.241 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 96829-59-3 (Lipstatin)
  • Hazard Symbols
  • Synonyms L-Leucine,N-formyl-, (1S,3Z,6Z)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-3,6-dodecadienylester (9CI);L-Leucine, N-formyl-,1-[(3-hexyl-4-oxo-2-oxetanyl)methyl]-3,6-dodecadienyl ester, [2S-[2a(1R*,3Z,6Z),3b]]-;(-)-Lipstatin;levocloperastine fendizoate;
  • PSA 81.70000
  • LogP 7.46070

Synthetic route

N-formyl-L-leucine
5338-45-4, 44978-39-4, 89921-44-8, 6113-61-7

N-formyl-L-leucine

4-<(4Z,7Z)-2-hydroxytrideca-4,7-dienyl>-3-hexyloxetan-2-one
108102-73-4

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

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1.5h; 0 deg C to RT;50%
(Z)-non-3-en-1-ol
10340-23-5

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

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
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
View Scheme
(Z)-3-nonenal
31823-43-5

(Z)-3-nonenal

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
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
View Scheme
(3Z)-1-bromo-3-nonene
136695-81-3, 60705-54-6

(3Z)-1-bromo-3-nonene

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / acetonitrile / 48 h / Heating
2: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
3: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C
4: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
5: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
6: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
7: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
(Z)-3-nonenal diisopropyl acetal
120018-49-7

(Z)-3-nonenal diisopropyl acetal

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating
2: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C
3: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT
4: 100 percent / acetonitrile / 48 h / Heating
5: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
6: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C
7: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
8: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
9: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
10: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
[(3Z)-3-nonen-1-yl]triphenylphosphonium bromide
85924-42-1

[(3Z)-3-nonen-1-yl]triphenylphosphonium bromide

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
2: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C
3: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
4: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
5: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
6: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
hexanal
66-25-1

hexanal

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 100 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
2: p-TsOH / H2O; tetrahydrofuran / 0.17 h / Heating
3: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C
4: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT
5: 100 percent / acetonitrile / 48 h / Heating
6: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT
7: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C
8: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
9: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
10: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
11: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
(R)-(Z,Z)-3-<(tert-Butyldimethylsilyl)oxy>-5,8-tetradecadienal
151509-74-9

(R)-(Z,Z)-3-<(tert-Butyldimethylsilyl)oxy>-5,8-tetradecadienal

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
2: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
3: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
4: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
Methyl (R)-(Z,Z)-3-<(tert-butyldimethylsilyl)oxy>-5,8-tetradecadienoate
151509-75-0

Methyl (R)-(Z,Z)-3-<(tert-butyldimethylsilyl)oxy>-5,8-tetradecadienoate

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C
2: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C
3: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
4: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
5: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
3-Hexyl-4-((4Z,7Z)-(R)-2-hydroxy-trideca-4,7-dienyl)-3-trimethylsilanyl-oxetan-2-one

3-Hexyl-4-((4Z,7Z)-(R)-2-hydroxy-trideca-4,7-dienyl)-3-trimethylsilanyl-oxetan-2-one

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
2: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
4-((4Z,7Z)-2-<1,1-dimethylethyl(dimethyl)silyloxy>trideca-4,7-dienyl)-3-trimethylsilyl-3-hexyloxetan-2-one

4-((4Z,7Z)-2-<1,1-dimethylethyl(dimethyl)silyloxy>trideca-4,7-dienyl)-3-trimethylsilyl-3-hexyloxetan-2-one

(-)-lipstatin
96829-59-3

(-)-lipstatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT
2: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C
3: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT
View Scheme
(-)-lipstatin
96829-59-3

(-)-lipstatin

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

Orlistat

Conditions
ConditionsYield
With sodium tetrahydroborate; (R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine cobalt; copper(l) chloride In acetonitrile at 15℃; Temperature; Reagent/catalyst; Inert atmosphere;95.2%
carbon palladium In ethanol
(-)-lipstatin
96829-59-3

(-)-lipstatin

1-(3-hexyl-4-oxo-oxetan-2-yl)tridecan-2-yl 2-formylamino-4-methylpentanoate

1-(3-hexyl-4-oxo-oxetan-2-yl)tridecan-2-yl 2-formylamino-4-methylpentanoate

Conditions
ConditionsYield
Stage #1: (-)-lipstatin With pyrographite In methanol; H20 for 0.5h;
Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; water under 3677.86 Torr; for 8h;
Stage #1: (-)-lipstatin With pyrographite In H20; isopropyl alcohol for 0.5h;
Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; water under 2942.29 Torr; for 6h;
Stage #1: (-)-lipstatin With pyrographite In H20; ethanol for 0.5h;
Stage #2: With hydrogen; palladium 10% on activated carbon In methanol; water under 2206.72 Torr; for 5h;

(-)-Lipstatin Specification

The IUPAC name of (-)-Lipstatin is [(2S,4E,7E)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl](2S)-2-formamido-3-methylpentanoate. With the CAS registry number 96829-59-3, it is also named as L-Leucine, N-formyl-, 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)-3,6-dodecadienyl ester, (2S-(2alpha(1R*,3Z,6Z),3beta))-. (-)-Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product, and was first isolated from the Actinobacterium Streptomyces toxytricini.

The other characteristics of (-)-Lipstatin can be summarized as: (1)ACD/LogP: 6.19; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8; (4)ACD/LogD (pH 7.4): 8; (5)ACD/BCF (pH 5.5): 768618; (6)ACD/BCF (pH 7.4): 768618; (7)ACD/KOC (pH 5.5): 568279; (8)ACD/KOC (pH 7.4): 568279; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 21; (12)Index of Refraction: 1.485; (13)Molar Refractivity: 141.695 cm3; (14)Molar Volume: 494.786 cm3; (15)Polarizability: 56.172×10-24 cm3; (16)Surface Tension: 36.427 dyne/cm; (17)Enthalpy of Vaporization: 92.853 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Rotatable Bond Count: 21; (20)Tautomer Count: 4; (21)Exact Mass: 491.361074; (22)MonoIsotopic Mass: 491.361074; (23)Topological Polar Surface Area: 81.7; (24)Heavy Atom Count: 35; (25)Complexity: 660.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(O[C@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)C\C=C/C\C=C/CCCCC)[C@@H](NC=O)CC(C)C
2. InChI:InChI=1/C29H49NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h12-13,15-16,22-27H,5-11,14,17-21H2,1-4H3,(H,30,31)/b13-12-,16-15-/t24-,25-,26-,27-/m0/s1 
3. InChIKey:OQMAKWGYQLJJIA-CUOOPAIEBU 

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