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96829-59-3

96829-59-3

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96829-59-3 Usage

Uses

Different sources of media describe the Uses of 96829-59-3 differently. You can refer to the following data:
1. Lipstatin, a potent inhibitor of the pancreas lipase, is reported to be useful in the treatment and/or prevention of obesity and related diseases.
2. Lipstatin is a potent irreversible inhibitor of pancreatic lipase, produced by Streptomyces toxytricini and first reported in 1987. In vivo, lipstatin acts to block the absorption of triglycerides while allowing fatty acid absorption. The tetrahydro analogue of lipstatin, orlistat, although less potent, was developed for the treatment of obesity.

Check Digit Verification of cas no

The CAS Registry Mumber 96829-59-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,6,8,2 and 9 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 96829-59:
(7*9)+(6*6)+(5*8)+(4*2)+(3*9)+(2*5)+(1*9)=193
193 % 10 = 3
So 96829-59-3 is a valid CAS Registry Number.
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

96829-59-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name [(2S,4E,7E)-1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl] (2S)-2-formamido-3-methylpentanoate

1.2 Other means of identification

Product number -
Other names (2S,3S,5S,7Z,10Z)-5-[(S)-2-formamido-4-methyl-valeryloxy]-2-hexyl-3-hydroxy-7,10-hexadecadienoic acid lactone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:96829-59-3 SDS

96829-59-3Synthetic 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;

96829-59-3Relevant articles and documents

An Approach to the Syntheiss of (-)-Lipstatin by Wittig Reaction and Lewis Acid-promoted Cycloaddition

Pons, Jean-Marc,Pommier, Agnes,Lerpiniere, Joan,Kocienski, Philip

, p. 1549 - 1552 (2007/10/02)

The β-lactone moiety of (-)-lipstatin 1, a potent inhibitor of pancreatic lipase, is prepared via a Lewis acid-promoted cycloaddition between hexyltrimethylsilyl ketene 3 and the (Z,Z)-dienic aldehyde 4, obtained from hexenal by two stereoselective Wittig reactions.

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