5-Hexenoic acid, 6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3S,4S,5E)-

Base Information

• Chemical Name: 5-Hexenoic acid, 6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3S,4S,5E)-
• CAS No.: 87081-56-9
• Molecular Formula: C₁₈H₂₃ClO₅
• Molecular Weight: 354.831
• DSSTox Substance ID: DTXSID401113353
• Nikkaji Number: J96.939G
• Wikidata: Q104986618
• Metabolomics Workbench ID: 97877
• ChEMBL ID: CHEMBL1094280
• Mol file: 87081-56-9.mol

Synonyms:87081-56-9;5-Hexenoic acid, 6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3S,4S,5E)-;(-)-oudemansin B;C18H23ClO5;CHEMBL1094280;C18-H23-Cl-O5;DTXSID401113353;Methyl (2E,3S,4S,5E)-6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-5-hexenoate

Chemical Property of 5-Hexenoic acid, 6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3S,4S,5E)-

Chemical Property:

• Vapor Pressure: 5.57E-09mmHg at 25°C
• Boiling Point: 469.3°Cat760mmHg
• Flash Point: 166.3°C
• PSA: 53.99000
• Density: 1.149g/cm³
• LogP: 3.71620
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 354.1234015
• Heavy Atom Count: 24
• Complexity: 449

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C=CC1=CC(=C(C=C1)Cl)OC)OC)C(=COC)C(=O)OC
• Isomeric SMILES: C[C@H]([C@H](/C=C/C1=CC(=C(C=C1)Cl)OC)OC)/C(=C\OC)/C(=O)OC

Technology Process of 5-Hexenoic acid, 6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3S,4S,5E)-

There total 9 articles about 5-Hexenoic acid, 6-(4-chloro-3-methoxyphenyl)-4-methoxy-2-(methoxymethylene)-3-methyl-, methyl ester, (2E,3S,4S,5E)- 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:

(E)-(3S,4S)-6-(4-Chloro-3-methoxy-phenyl)-2-formyl-4-methoxy-3-methyl-hex-5-enoic acid methyl ester + dimethyl sulfate (77-78-1) → (+/-)-oudemansin B (87081-56-9,107243-74-3)

Guidance literature:

With potassium carbonate; In acetone; for 12h; Yield given;

DOI:10.1021/jo00228a028

Reference yield:

C20H17ClLiO2P → oudemansin B (87081-56-9,107243-74-3)

Guidance literature:

Multi-step reaction with 7 steps

2: LiBH₄ / tetrahydrofuran / 0 °C

3: 1.) 9-BBN; 2.) H₂O₂ / 1.) THF, O deg C

4: Jones

5: diethyl ether

6: LDA

7: K₂CO₃

With lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(00)84551-7

Reference yield:

(3R,4S)-1-(4-Chloro-3-methoxy-phenyl)-1-(diphenyl-phosphinoyl)-3-methoxy-4-methyl-hex-5-en-2-one (109864-22-4,109956-77-6) → oudemansin B (87081-56-9,107243-74-3)

Guidance literature:

Multi-step reaction with 6 steps

1: LiBH₄ / tetrahydrofuran / 0 °C

2: 1.) 9-BBN; 2.) H₂O₂ / 1.) THF, O deg C

3: Jones

4: diethyl ether

5: LDA

6: K₂CO₃

With lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(00)84551-7

upstream raw materials:

(E)-(3S,4R)-6-(4-Chloro-3-methoxy-phenyl)-4-methoxy-3-methyl-hex-5-enoic acid

(E)-(3S,4S)-6-(4-Chloro-3-methoxy-phenyl)-2-[1-hydroxy-meth-(Z)-ylidene]-4-methoxy-3-methyl-hex-5-enoic acid methyl ester

dimethyl sulfate

(3R,4S)-1-(4-Chloro-3-methoxy-phenyl)-1-(diphenyl-phosphinoyl)-3-methoxy-4-methyl-hex-5-en-2-one