methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

Base Information

• Chemical Name: methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate
• CAS No.: 94120-03-3
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.262
• Wikidata: Q75056811
• Metabolomics Workbench ID: 118880
• Mol file: 94120-03-3.mol

Synonyms:citreodiol;epi-citreodiol

Chemical Property of methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

Chemical Property:

• Vapor Pressure: 1.35E-06mmHg at 25°C
• Boiling Point: 358.9°Cat760mmHg
• Flash Point: 134.6°C
• PSA: 66.76000
• Density: 1.092g/cm³
• LogP: 0.79370
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 214.12050905
• Heavy Atom Count: 15
• Complexity: 280

Purity/Quality:

Citreodiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C(C)(C=CC=C(C)C(=O)OC)O)O
• Isomeric SMILES: C[C@H]([C@@](C)(/C=C/C=C(\C)/C(=O)OC)O)O
• Uses: Citreodiol is a natural product that acts as a key intermediate of lankacidin biosynthesis. It can also be derived from the mycelium of Penicillium citreo-viride B.

Technology Process of methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

There total 4 articles about methyl (2E,4E,6R,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate 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:

(2E,4E)-5-((4R,5R)-4,5-Dimethyl-2-oxo-[1,3]dioxolan-4-yl)-2-methyl-penta-2,4-dienoic acid methyl ester → citreodiol, <6R, 7R>-6,7-dihydroxy-2,6-dimethyloct-2,4-dienoic acid methyl ester (94120-03-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1038/ja.2014.160

Reference yield:

(2R,3S,4S,5R)-6-Methoxy-2,3-dimethyl-tetrahydro-pyran-3,4,5-triol (102271-41-0) → (+)-citreodiol (94120-03-3,94136-10-4)

Guidance literature:

DOI:10.1016/S0040-4039(01)81515-X

Reference yield:

(4S,5S)-4-(2-carbethoxyethenyl)-2,2,4,5-tetramethyl-1,3-dioxolane (106622-90-6) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → (-)-epicitreodiol (94120-03-3,94136-10-4)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(01)81515-X

upstream raw materials:

(4R,5S)-4-(2-carbethoxyethenyl)-2,2,4,5-tetramethyl-1,3-dioxolane

methyl 2-(triphenylphosphoranylidene)propionate

(2R,3S,4S,5R)-6-Methoxy-2,3-dimethyl-tetrahydro-pyran-3,4,5-triol

(4S,5S)-4-(2-carbethoxyethenyl)-2,2,4,5-tetramethyl-1,3-dioxolane