methyl 4-[(2S,3S)-3-[(1E,3E)-5-oxopenta-1,3-dienyl]oxiran-2-yl]butanoate

Base Information

• Chemical Name: methyl 4-[(2S,3S)-3-[(1E,3E)-5-oxopenta-1,3-dienyl]oxiran-2-yl]butanoate
• CAS No.: 73958-00-6
• Molecular Formula: C12H16 O4
• Molecular Weight: 224.257
• DSSTox Substance ID: DTXSID701154285
• Nikkaji Number: J569.928B,J877.201K
• Mol file: 73958-00-6.mol

Synonyms:73958-00-6;DTXSID701154285;(2S)-3alpha-(5-Oxo-1,3-pentadienyl)oxirane-2beta-butanoic acid methyl ester;3alpha-[(1E,3E)-5-Oxo-1,3-pentadienyl]oxirane-2beta-butanoic acid methyl ester;Methyl (2S,3S)-3-[(1E,3E)-5-oxo-1,3-pentadien-1-yl]-2-oxiranebutanoate;methyl 4-((2S,3S)-3-((1E,3E)-5-oxopenta-1,3-dienyl)oxiran-2-yl)butanoate

Chemical Property of methyl 4-[(2S,3S)-3-[(1E,3E)-5-oxopenta-1,3-dienyl]oxiran-2-yl]butanoate

Chemical Property:

• PSA: 55.90000
• LogP: 1.40840
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 224.10485899
• Heavy Atom Count: 16
• Complexity: 293

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCC1C(O1)C=CC=CC=O
• Isomeric SMILES: COC(=O)CCC[C@H]1[C@@H](O1)/C=C/C=C/C=O

Technology Process of methyl 4-[(2S,3S)-3-[(1E,3E)-5-oxopenta-1,3-dienyl]oxiran-2-yl]butanoate

There total 84 articles about methyl 4-[(2S,3S)-3-[(1E,3E)-5-oxopenta-1,3-dienyl]oxiran-2-yl]butanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C26H22O8 (55797-81-4,105453-39-2) → 4-[(2S,3S)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester (73958-00-6,76738-48-2,77341-38-9,79356-64-2,79356-67-5,82442-92-0,92009-26-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / benzoic acid / 1,2-dimethoxy-ethane / 4 h / Heating

2: 100 percent / H₂SO₄ / 3 h / 23 °C

3: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

4: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

5: 99 percent / dry hydroden chloride / 72 h / 23 °C

6: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

7: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

8: 96 percent / Collins reagent / CH₂Cl₂ / 0.25 h / 23 °C

9: 2.) aq. NaHCO₃ / tetrahydrofuran / 1 h / -78 °C

10: NEt₃ / CH₂Cl₂ / 0.25 h / -45 °C

11: phosphate buffer / -45 - 0 °C

With pyridine; hydrogenchloride; amalgamated zinc; phosphate buffer; Collins oxidation agent; sulfuric acid; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane;

DOI:10.1021/ja00524a045

Reference yield:

(-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester (73957-99-0) → (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / Py₂*CrO₃; 4 Angstroem molecular sieves / CH₂Cl₂

2: CH₂Cl₂ / 15 h

3: I₂ / CH₂Cl₂ / 1 h

With CrO₃*2Py; 4 A molecular sieve; iodine; In dichloromethane; 1: Oxidation / 2: Olefination / 3: Isomerization;

DOI:10.1002/1099-0690(200009)2000:17<2991::AID-EJOC2991>3.0.CO;2-H

Reference yield:

[(4R,5S)-5-((Z)-3-[1,3]Dioxan-2-yl-propenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (85612-85-7) → (5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester (73958-00-6)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; chromium(VI) oxide; hydrogen; iodine; oxygen; potassium carbonate; ozone; triethylamine; trifluoroacetic acid; platinum(IV) oxide; In dichloromethane; water; ethyl acetate;

DOI:10.1021/ja00349a053

upstream raw materials:

3-Formylallyl(triphenyl)arsonium bromide

(+)-(S,R-trans)-3-formyloxiranebutanoic acid methyl ester

(2E)-4-triphenylphosphoranylidene-2-butenal

(-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester

Downstream raw materials:

Leukotriene A₄ methyl ester

4-[(2S,3S)-((1E,3E,5Z,8Z)-3-Tetradeca-1,3,5,8-tetraenyl)-oxiranyl]-butyric acid methyl ester

(+/-)-16-oxa-14,15-dinor-13,16-inter-o-phenyleneleucotriene A₄ methyl ester

leukotriene E4

Refernces

• 1、 Rodriguez, Ana,Nomen, Miguel,Spur, Bernd W.,Godfroid, Jean-Jacques,Lee, Tak H.. "Total synthesis of leukotrienes from butadiene". . p. 2991 - 3000. Retrieved 2007/10/03.
• 2、 Wang, Yanfang,Li, Jincui,Wu, Yulin,Huang, Yaozeng,Shi, Lilan,Yang, Jianhua. "A FACILE STEREOSELECTIVE SYNTHESIS OF LEUKOTRIENE A4(LTA4) METHYL ESTER". . p. 4583 - 4584. Retrieved 2007/10/02.