CAS No.73466-12-3,(-)-LEUKOTRIENE A4 METHYL ESTER Suppliers

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2-Oxiranebutanoic acid,3-(1E,3E,5Z,8Z)-1,3,5,8-tetradecatetraen-1-yl-, methyl ester, (2S,3S)-Appearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical resear

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Synthetic route

: 82393-41-7
<(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

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

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

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

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

: 71548-17-9, 72059-45-1, 74497-09-9, 76375-76-3, 77341-35-6, 114129-55-4, 114129-56-5, 114129-57-6
6-epi-Leukotriene A4

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

Conditions	Yield
In diethyl ether at 0℃; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 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

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;

...Expand

: 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

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

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

...Expand

: 73957-99-0
(-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

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

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

: 76871-82-4
7-acetoxy-(5S,6S)-epoxyheptanoic acid methyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 69 percent / K2CO3; Na2SO4 / methanol / 0.17 h / 20 °C 2: 68 percent / Py2*CrO3; 4 Angstroem molecular sieves / CH2Cl2 3: CH2Cl2 / 15 h 4: I2 / CH2Cl2 / 1 h 5: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme

: 73958-00-6, 76738-48-2, 77341-38-9, 79356-64-2, 79356-67-5, 82442-92-0, 92009-26-2
(5S,6S)-epoxy-10-formyl-(9E)-decadienoic acid methyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: I2 / CH2Cl2 / 1 h 2: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: iodine 2: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide View Scheme

: 7-acetoxy-(5S,6S)-epoxyheptanoic acid

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: diethyl ether / 0.08 h / 0 °C 2: 69 percent / K2CO3; Na2SO4 / methanol / 0.17 h / 20 °C 3: 68 percent / Py2*CrO3; 4 Angstroem molecular sieves / CH2Cl2 4: CH2Cl2 / 15 h 5: I2 / CH2Cl2 / 1 h 6: 63 percent / nBuLi; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C View Scheme

: 31333-13-8
3-nonyn-1-ol

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 96.4 percent / hydrogen, quinoline / Lindlar catalyst / hexane / 1.25 h 2: 97.1 percent / pyridine / 1.5 h / 0 - 5 °C 3: 95 percent / sodium iodide / acetone / 67 h / Ambient temperature 4: 11.2 g / benzene / 43 h / 80 °C 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

: 10340-23-5
(Z)-non-3-en-1-ol

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 97.1 percent / pyridine / 1.5 h / 0 - 5 °C 2: 95 percent / sodium iodide / acetone / 67 h / Ambient temperature 3: 11.2 g / benzene / 43 h / 80 °C 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

: 85612-85-7
[(4R,5S)-5-((Z)-3-[1,3]Dioxan-2-yl-propenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 40.8 g / pyridine / 3 h / 5 °C 2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 4: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 5: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 6: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 9: 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 9 steps 1: 40.8 g / pyridine / 3 h / 5 °C 2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 4: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 5: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 6: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 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 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 9 steps
1: 40.8 g / pyridine / 3 h / 5 °C
2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C
4: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
5: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
6: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
8: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
9: 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 9 steps
1: 40.8 g / pyridine / 3 h / 5 °C
2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C
4: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
5: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
6: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
8: 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
9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 72297-08-6
3-cis-nonene-1-yl-p-toluenesulfonate

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / sodium iodide / acetone / 67 h / Ambient temperature 2: 11.2 g / benzene / 43 h / 80 °C 3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

: 13224-97-0, 13224-98-1, 13224-99-2, 13225-00-8, 13225-01-9, 13225-02-0, 18465-50-4, 87068-63-1
(1’R)-(-)-4,6-O-ethylidene-D-glucose

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: NaIO4, aq. sodium hydroxide / H2O / 0.25 h / 5 - 10 °C / pH 4 2: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 3: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 4: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 5: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 6: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 7: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 8: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 9: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 10: 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 10 steps 1: NaIO4, aq. sodium hydroxide / H2O / 0.25 h / 5 - 10 °C / pH 4 2: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 3: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 4: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 5: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 6: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 7: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 8: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 9: 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 10: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 10 steps
1: NaIO4, aq. sodium hydroxide / H2O / 0.25 h / 5 - 10 °C / pH 4
2: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C
3: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C
4: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
5: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
6: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
7: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
8: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
9: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
10: 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 10 steps
1: NaIO4, aq. sodium hydroxide / H2O / 0.25 h / 5 - 10 °C / pH 4
2: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C
3: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C
4: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
5: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
6: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
7: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
8: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
9: 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
10: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 77332-97-9
(+)--6-<2-<(benzoyloxy)-1-hydroxy>ethyl>tetrahydro-2H-pyran-2-one

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 2: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 5: 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 5 steps 1: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 2: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 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 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 5 steps
1: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
2: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
4: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
5: 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 5 steps
1: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
2: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
4: 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
5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 77332-98-0
Benzoic acid (R)-2-methanesulfonyloxy-2-((S)-6-oxo-tetrahydro-pyran-2-yl)-ethyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 4: 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 4 steps 1: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 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 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 4 steps
1: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
3: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
4: 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 4 steps
1: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
3: 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
4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 77333-01-8
(+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 2: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 3: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 6: 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 6 steps 1: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 2: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 3: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 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 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 6 steps
1: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
2: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
3: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
5: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
6: 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 6 steps
1: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
2: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
3: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
5: 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
6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 77333-00-7, 85648-04-0
(+)-(4R-cis)-2,2-dimethyl-5-<3-(1,3-dioxan-2-yl)-1-propyl>-1,3-dioxolane-4-methanol benzoate

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 2: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 3: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 4: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 7: 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 7 steps 1: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 2: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 3: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 4: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 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 7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 7 steps
1: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C
2: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
3: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
4: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
6: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
7: 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 7 steps
1: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C
2: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
3: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
4: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
6: 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
7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 77332-94-6, 77398-80-2
(+)-(4R-cis)(Z)-2,2-dimethyl-5-<3-(1,3-dioxan-2-yl)-1-propenyl>-1,3-dioxolane-4-methanol benzoate

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 3: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 4: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 5: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 8: 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 8 steps 1: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C 3: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C 4: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C 5: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 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 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 8 steps
1: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
2: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C
3: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
4: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
5: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
7: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
8: 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 8 steps
1: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
2: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C
3: 71.9 percent / trifluoroacetic acid / H2O / 3.5 h / 0 °C
4: 5.9 g / triethylamine / CH2Cl2 / 0.75 h / -5 - 0 °C
5: 79.3 percent / potassium carbonate / 7.5 h / 3 - 5 °C
6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
7: 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
8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 72297-09-7
(3Z)-3-nonenyliodide

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 11.2 g / benzene / 43 h / 80 °C 2: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

: 85612-90-4
(2R,4S,5R)-4-((E)-3-[1,3]Dioxan-2-yl-propenyl)-2-methyl-[1,3]dioxan-5-ol

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 2: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 4: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 5: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 8: 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 8 steps 1: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 2: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 3: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 4: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 5: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 7: 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 8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 8 steps
1: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C
2: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
3: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
4: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
5: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
7: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
8: 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 8 steps
1: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C
2: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
3: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
4: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
5: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
6: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
7: 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
8: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 85612-93-7
Methanesulfonic acid (R)-2-hydroxy-1-((S)-6-oxo-tetrahydro-pyran-2-yl)-ethyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 4: 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 4 steps 1: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 3: 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 4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 4 steps
1: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
3: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
4: 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 4 steps
1: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
2: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
3: 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
4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 85612-91-5
(-)-(2R,4S,5R)-4-<3-(1,3-dioxan-2-yl)propyl>-2-methyl-1,3-dioxan-5-ol methanesulfonate

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 2: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 3: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 6: 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 6 steps 1: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 2: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 3: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 5: 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 6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 6 steps
1: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
2: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
3: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
5: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
6: 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 6 steps
1: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
2: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
3: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
4: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
5: 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
6: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 85612-89-1
(2R,4S,5R)(E)-4-<3-(1,3-dioxan-2-yl)-1-propenyl>-2-methyl-1,3-dioxan-5-ol methanesulfonate

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 3: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 4: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 7: 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 7 steps 1: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 2: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 3: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 4: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 6: 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 7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 7 steps
1: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
2: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
3: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
4: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
6: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
7: 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 7 steps
1: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
2: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
3: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
4: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
5: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
6: 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
7: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 85612-92-6
(-)-(2R,4S,5R)-2-methyl-5-<(methylsulfonyl)oxy>-1,3-dioxane-4-butanoic acid 3-hydroxypropyl ester

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 2: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 5: 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 5 steps 1: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 2: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 4: 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 5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 5 steps
1: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
2: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
4: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
5: 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 5 steps
1: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
2: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
3: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
4: 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
5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 70377-89-8
(1'R)-(-)-2,4-O-ethylidene-D-erythrose

: 73466-12-3
Leukotriene A4 methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 2: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 3: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 4: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 5: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 6: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h 9: 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 9 steps 1: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C 2: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C 3: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature 4: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C 5: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C 6: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C 7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h 8: 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 9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min View Scheme

Yield

Multi-step reaction with 9 steps
1: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C
2: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C
3: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
4: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
5: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
6: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
8: 2.) iodine / 1) CH2Cl2, room temperature, 1 h; 2) CH2Cl2, room temperature, 2.5 h
9: 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 9 steps
1: 4.7 g / tetrahydrofuran / 0.33 h / -30 °C
2: 2.8 g / triethylamine / CH2Cl2 / 0.75 h / 0 - 5 °C
3: 76.3 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature
4: 54.5 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C
5: trifluoroacetic acid, water / 5.5 h / 0 - 5 °C
6: 105 mg / potassium carbonate / 5.5 h / 0 - 5 °C
7: 69.7 percent / pyridine, chromium trioxide / CH2Cl2 / 1) 15 deg C, 15 - 20 min; 2) 15 deg C --> room temperature, 1 h
8: 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
9: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) HMPA, THF, hexane, -78 deg C, 15 min
View Scheme

: 18598-63-5
L-cysteine methyl ester hydrochloride

: 73466-12-3
Leukotriene A4 methyl ester

: 74448-22-9
leukotriene E4 dimethyl ester

Conditions

Conditions	Yield
With triethylamine In methanol; water for 1h; Ambient temperature; pH 9;	94%
With triethylamine In methanol for 5h; Ring cleavage; Condensation;	75%

: 73466-12-3
Leukotriene A4 methyl ester

: 75290-62-9
N-(trifluoroacetyl)-L-cysteinylglycine methyl ester

: 76322-44-6
N-trifluoroacetyl-leukotriene D4 dimethyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 4h; Ring cleavage; Condensation;	77%

: 73466-12-3
Leukotriene A4 methyl ester

: 135388-27-1
methyl 6-mercapto-3(E)-hexenoate

: 140215-33-4
(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-((E)-5-methoxycarbonyl-pent-3-enylsulfanyl)-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate In methanol for 3h; Ambient temperature;	71%

: 27025-41-8
Oxidized glutathione

: 73466-12-3
Leukotriene A4 methyl ester

: 73958-10-8
Leukotriene C4 methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 12h; Condensation; Ring cleavage;	55%

: 70-18-8
GLUTATHIONE

: 73466-12-3
Leukotriene A4 methyl ester

: (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine for 2h; Ambient temperature;

: 42302-17-0
3-Dimethylaminopropanethiol

: 73466-12-3
Leukotriene A4 methyl ester

: 83851-65-4
(7E,9E,11Z,14Z)-(5S,6R)-6-(3-Dimethylamino-propylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

: 20756-86-9
1-mercapto-5-carbomethoxy-pentane

: 73466-12-3
Leukotriene A4 methyl ester

: (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-(5-methoxycarbonyl-pentylsulfanyl)-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate In methanol

: 75290-61-8
N-Trifluoroacetylglutathione dimethyl ester

: 73466-12-3
Leukotriene A4 methyl ester

: 76695-80-2, 76740-25-5
(6E,8E,10E,14Z)-(S)-5-Hydroxy-12-{(R)-2-(methoxycarbonylmethyl-carbamoyl)-2-[(R)-4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-6,8,10,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With lithium perchlorate In tetrahydrofuran; diethyl ether at 23℃; for 12h; Yield given;

: 73466-12-3
Leukotriene A4 methyl ester

: 140215-41-4
methyl 6-mercapto-3(Z)-hexenoate

: 140215-33-4
(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-((Z)-5-methoxycarbonyl-pent-3-enylsulfanyl)-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate In methanol Ambient temperature;

: 73466-12-3
Leukotriene A4 methyl ester

: 83851-50-7
(S)-4-((R)-2-Mercapto-1-methoxycarbonyl-ethylcarbamoyl)-2-(2,2,2-trifluoro-acetylamino)-butyric acid methyl ester

: 83851-62-1, 84414-54-0
(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{(R)-2-methoxycarbonyl-2-[(S)-4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

: 73466-12-3
Leukotriene A4 methyl ester

: 80115-99-7
methyl 3-mercaptopropionylglycinate

: 80116-00-3
deamino LTD4 dimethyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;	4.2 mg

: 73466-12-3
Leukotriene A4 methyl ester

: 83851-49-4
3-mercaptopropionylglycinedimethylamide

: (7E,9E,11Z,14Z)-(5S,6R)-6-[2-(Dimethylcarbamoylmethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;	2.3 mg

: 73466-12-3
Leukotriene A4 methyl ester

: 83851-52-9
[(3-Mercapto-propyl)-(2,2,2-trifluoro-acetyl)-amino]-acetic acid methyl ester

: 83851-64-3
(7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{3-[methoxycarbonylmethyl-(2,2,2-trifluoro-acetyl)-amino]-propylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

: 73466-12-3
Leukotriene A4 methyl ester

: 83851-48-3
4-[(R)-2-Mercapto-1-(methoxycarbonylmethyl-carbamoyl)-ethylcarbamoyl]-butyric acid methyl ester

: (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-[(R)-2-(4-methoxycarbonyl-butyrylamino)-2-(methoxycarbonylmethyl-carbamoyl)-ethylsulfanyl]-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

: 73466-12-3
Leukotriene A4 methyl ester

: 83851-51-8
(S)-2-[(R)-3-Mercapto-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-pentanedioic acid dimethyl ester

: 83851-63-2
(S)-2-[(R)-3-[(2E,4E,6Z,9Z)-(R)-1-((S)-1-Hydroxy-4-methoxycarbonyl-butyl)-pentadeca-2,4,6,9-tetraenylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-propionylamino]-pentanedioic acid dimethyl ester

Conditions

Conditions	Yield
With triethylamine In methanol for 3h; Ambient temperature;

: 73466-12-3
Leukotriene A4 methyl ester

: L-cysteinylglycine

: (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol; water for 18h; Ambient temperature;

: 73466-12-3
Leukotriene A4 methyl ester

glutathione: glutathione

: 73958-10-8, 74841-70-6, 84823-29-0, 84823-30-3, 89461-60-9, 89461-61-0, 89461-62-1, 89461-63-2, 92009-28-4, 113830-70-9, 113830-71-0, 113830-72-1
(7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Conditions

Conditions	Yield
With triethylamine In methanol at 23℃; for 5h;

: 73466-12-3
Leukotriene A4 methyl ester

: 75715-89-8
leukotriene E4

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Et3N / methanol / 5 h 2: 82 percent / K2CO3 / methanol; H2O / 3.5 h / 0 °C View Scheme

: 73466-12-3
Leukotriene A4 methyl ester

: 73836-78-9
leukotriene D4

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / Et3N / methanol / 4 h 2: 82 percent / K2CO3 / methanol; H2O / 3.5 h / 0 °C View Scheme

: 73466-12-3
Leukotriene A4 methyl ester

: 73466-14-5, 74841-69-3, 76738-45-9, 79026-71-4, 79026-72-5, 80629-45-4, 82468-64-2, 84823-19-8, 84823-20-1, 87391-79-5, 92009-30-8, 92418-31-0, 92418-46-7, 72025-60-6
(7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 55 percent / Et3N / methanol / 12 h 2: 84 percent / K2CO3 / methanol; H2O / 3.5 h / 20 °C View Scheme

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Hazard Codes	F,Xn,N
Risk Statements	11-36/37/38-48/20-51/53-62-65-67
Safety Statements	9-16-29-33-36/37-61-62
RIDADR	UN 1208 3/PG 2
WGK Germany	2

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