(2R,3R,5Z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid

Base Information Edit

Chemical Name:(2R,3R,5Z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid
CAS No.:13588-16-4
Molecular Formula:C10H16O5
Molecular Weight:216.234
Hs Code.:2918199090
UNII:AXN0570QIE
Nikkaji Number:J12.026J,J15.473C
Mol file:13588-16-4.mol

Synonyms:necic acid;necic acid, (E)-isomer

Suppliers and Price of (2R,3R,5Z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,5Z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid Edit

Chemical Property:

Melting Point:145-146°
Boiling Point:466.7±45.0 °C(Predicted)
PKA:3.95±0.27(Predicted)
PSA：94.83000
Density:1.241±0.06 g/cm3(Predicted)
LogP:0.87910
XLogP3:0.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:216.09977361
Heavy Atom Count:15
Complexity:294

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC=C(CC(C)C(C)(C(=O)O)O)C(=O)O
Isomeric SMILES:C/C=C(/C[C@@H](C)[C@](C)(C(=O)O)O)\C(=O)O

Technology Process of (2R,3R,5Z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid

There total 21 articles about (2R,3R,5Z)-5-ethylidene-2-hydroxy-2,3-dimethylhexanedioic acid 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: 97.0%

: 520-65-0
rosmarinine

: 469-45-4,6582-63-4,6703-97-5,6883-40-5,10407-68-8,10407-69-9,10407-70-2,10407-71-3,10407-73-5,13588-16-4,86747-28-6,86747-29-7
Senecinsaeure

: 520-61-6
(-)-Rosmarinecine

Guidance literature:: With barium dihydroxide;

Reference yield:

: 81165-20-0
(2R,3R)-5-(1-Hydroxy-ethyl)-2,3-dimethyl-6-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester

: 469-45-4,6582-63-4,6703-97-5,6883-40-5,10407-68-8,10407-69-9,10407-70-2,10407-71-3,10407-73-5,13588-16-4,86747-28-6,86747-29-7
(+/-)-integerrinecic acid

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N, 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂

2: 96 percent / LiOH*H₂O / tetrahydrofuran / 0 °C

3: strong alkali

With lithium hydroxide; strong alkali; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00322a036

Reference yield:

: 81165-19-7,105927-22-8
5-methoxycarbonyl-4,5-cis-dimethyl-5-peantanolide

: 469-45-4,6582-63-4,6703-97-5,6883-40-5,10407-68-8,10407-69-9,10407-70-2,10407-71-3,10407-73-5,13588-16-4,86747-28-6,86747-29-7
(+/-)-integerrinecic acid

Guidance literature:: Multi-step reaction with 4 steps

1: BuLi, diisopropylamine / tetrahydrofuran; hexane / 1 h / -40 - -30 °C

2: Et₃N, 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂

3: 96 percent / LiOH*H₂O / tetrahydrofuran / 0 °C

4: strong alkali

With lithium hydroxide; n-butyllithium; strong alkali; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja00322a036