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CAS No.: | 96829-59-3 |
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Name: | Lipstatin |
Article Data: | 1 |
Molecular Structure: | |
Formula: | C29H49NO5 |
Molecular Weight: | 491.712 |
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; |
EINECS: | 619-246-0 |
Density: | 0.994 g/cm3 |
Boiling Point: | 627.402 °C at 760 mmHg |
Flash Point: | 333.241 °C |
PSA: | 81.70000 |
LogP: | 7.46070 |
N-formyl-L-leucine
4-<(4Z,7Z)-2-hydroxytrideca-4,7-dienyl>-3-hexyloxetan-2-one
(-)-lipstatin
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1.5h; 0 deg C to RT; | 50% |
(Z)-non-3-en-1-ol
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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
(-)-lipstatin
Conditions | Yield |
---|---|
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 |
(-)-lipstatin
Conditions | Yield |
---|---|
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 |
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