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| CAS No.: | 73466-12-3 | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Name: | (-)-LEUKOTRIENE A4 METHYL ESTER | ||||||||||
| Article Data: | 20 | ||||||||||
| Molecular Structure: | |||||||||||
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| Formula: | C21H32 O3 | ||||||||||
| Molecular Weight: | 332.483 | ||||||||||
| Synonyms: | Oxiranebutanoicacid, 3-(1,3,5,8-tetradecatetraenyl)-, methyl ester, [2S-[2a,3b(1E,3E,5Z,8Z)]]-; Oxiranebutanoic acid,3-(1E,3E,5Z,8Z)-1,3,5,8-tetradecatetraenyl-, methyl ester, (2S,3S)- (9CI);(-)-LTA4 methyl ester; LTA4 methyl ester; Leukotriene A methyl ester;Leukotriene A4 methyl ester | ||||||||||
| Hazard Symbols: | F,Xn,N | ||||||||||
| Risk Codes: | 11-36/37/38-48/20-51/53-62-65-67 | ||||||||||
| Safety: |
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| PSA: | 38.83000 | ||||||||||
| LogP: | 5.29230 | ||||||||||
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<(Z)-3-nonenyl>triphenyl phosphonium tosylate
- 73958-00-6
(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester
- 73466-12-3
Leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| With n-butyllithium In tetrahydrofuran at -78℃; | 90% |
- 73958-00-6
(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester
- 73958-09-5
Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide
- 73466-12-3
Leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; | 88% |
- 72297-07-5
<(3Z)-nonen-1-yl>triphenylphosphonium iodide
- 73958-00-6
(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester
- 73466-12-3
Leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Wittig reaction; | 63% |
| With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide | |
| With n-butyllithium 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min; Yield given. Multistep reaction; |
- 75331-81-6
(S)-5-hydroperoxy-6-trans,8,11,14-cis-eicosatetraenoic acid methyl ester
A
- 73466-12-3
Leukotriene A4 methyl ester
B
- 74785-00-5
methyl (6E,8Z,11Z,14Z)-5-oxo-6,8,11,14-eicosatetraenoate
| Conditions | Yield |
|---|---|
| With 1,2,2,6,6-pentamethylpiperidine; trifluoromethanesulfonic acid anhydride In diethyl ether; dichloromethane at -110℃; for 0.666667h; | A 25% B n/a |
- 186581-53-3, 908094-01-9
diazomethane
A
- 73466-12-3
Leukotriene A4 methyl ester
B
- 76738-49-3
5S,6R-6-epi-Leukotriene A4 methyl ester
C
- 79356-68-6
5R,6S-6-epi-Leukotriene A4 methyl ester
D
- 79356-65-3
5-epi-6-epi-leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| In diethyl ether at 0℃; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
- 82442-92-0
methyl 5(S),6(S)-oxido-11-oxo-7-cis-9-trans-undecadienoate
- 73958-09-5
Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide
A
- 73466-12-3
Leukotriene A4 methyl ester
B
- 82467-14-9
7-cis-leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 0.333333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
- 73958-00-6
(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester
- 75415-25-7
triphenyl <(Z)-non-3-en-1-yl>phosphonium chloride
- 73466-12-3
Leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| Yield given; |
- 118333-88-3
(5S,6S)-epoxy-11,14-eicosadiyne-7E,9E-dienoate
A
- 73466-12-3
Leukotriene A4 methyl ester
B
- 82850-12-2
13,14-dehydro-leukotriene A4 methyl ester
C
- 118333-83-8
4-[(2S,3S)-((1E,3E,8Z)-3-Tetradeca-1,3,8-trien-5-ynyl)-oxiranyl]-butyric acid methyl ester
| Conditions | Yield |
|---|---|
| With pyridine; hydrogen; Lindlar's catalyst In hexane at 20℃; under 750.06 Torr; Yields of byproduct given; | A 5.5 mg B n/a C n/a |
| With pyridine; hydrogen; Lindlar's catalyst In hexane at 20℃; under 750.06 Torr; Yield given; | A 5.5 mg B n/a C n/a |
- 73957-99-0
(-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester
- 73466-12-3
Leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 68 percent / Py2*CrO3; 4 Angstroem molecular sieves / CH2Cl2 2: CH2Cl2 / 15 h 3: I2 / CH2Cl2 / 1 h 4: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme | |
| Multi-step reaction with 3 steps 1: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 2: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme | |
| Multi-step reaction with 3 steps 1: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 2: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme | |
| Multi-step reaction with 3 steps 1: 63 percent / CrO3/Py / CH2Cl2 2: 70 percent 3: 90 percent / n-BuLi / tetrahydrofuran / -78 °C View Scheme | |
| Multi-step reaction with 3 steps 1: 50 percent / Collins oxidation View Scheme |
- 73427-12-0
(+)-(S,R-trans)-3-formyloxiranebutanoic acid methyl ester
- 73466-12-3
Leukotriene A4 methyl ester
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: CH2Cl2 / 15 h 2: I2 / CH2Cl2 / 1 h 3: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme | |
| Multi-step reaction with 2 steps 1: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme | |
| Multi-step reaction with 2 steps 1: 1.) n-BuLi, 3.) triethylamine, methane sulfonyl chloride / 1) THF, hexane, -78 deg C, 1 h; 2) -78 deg C, 1.75 h, THF, hexane; 3) CH2Cl2, -45 deg C, 20 min 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme |
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