119008-08-1

Upstream product

• 108-05-4 vinyl acetate 
• 109296-10-8 4-hydroxy-trans-2-nonenal-dimethylacetal 
• 119008-07-0 (E)-(S)-1,1-Dimethoxy-non-2-en-4-ol 
• 119009-01-7 (E)-(R)-1,1-Dimethoxy-non-2-en-4-ol 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 110222-66-7 (2S,3R)-3-pentyloxirane-2-carbaldehyde 
• 693-25-4 n-pentylmagnesium bromide 
• 155555-68-3 (6R,7R,8R,9R)-7,8-O-isopropylidene-6,7,8,9-tetradecanetetraol 
• 155555-69-4 C₃₁H₄₂O₆ 
• 155485-49-7 C₂₈H₃₈O₆ 
• 159716-60-6 Benzoic acid (R)-1-((E)-3-oxo-propenyl)-hexyl ester 
• 159716-65-1 Benzoic acid (R)-1-((E)-3,3-dimethoxy-propenyl)-hexyl ester 
• 119092-07-8 Benzoic acid (R)-1-formyl-hexyl ester 

Downstream Products

• 128860-91-3 (E)-(R)-1-((4S,5S)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-yl)-oct-1-en-3-ol 

Relevant academic research and scientific papers

SORBIC ACID IRON TRICARBONYL COMPLEX AS RESOLVING AGENT. CHIRAL SYNTHESES OF 4-HYDROXY NONENAL AND CORIOLIC ACID.

The chiral iron tricarbonyl complex of sorbic acid 2 is an efficent resolving agent for allylic alcohol 3, which is a key intermediate in the preparation of most of the lipoxygenation products in n-6 position of polyunsaturated fatty acids.The synthesis of 4-hydroxy nonenal and methyl coriolate, in both enantiomeric forms, illustrates the potential of the method.

Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine

2,3-Epoxy-4-hydroxynonanal (EHN) is a potential product of lipid peroxidation that gives rise to genotoxic etheno adducts. We have synthesized all four stereoisomers of EHN and individually reacted them with 2′-deoxyguanosine. In addition to 1,N2-etheno-2′- deoxyguanosine, 12 stereoisomeric products were isolated and characterized by 1H NMR and circular dichroism spectroscopy. The stereochemical assignments were consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations. Reversed-phase HPLC conditions were developed that could separate most of the adduct mixture.

A practical synthesis of (R)- and (S)-(E)-4-hydroxyalk-2-enals, cytotoxic products of the microsomal lipid peroxidation

The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out via enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediates obtained from two diastereomeric diepoxide

Syntheses stereoselectives de metabolites hydroxyles d'acides gras polyinsatures

The E,Z dienol structure is characteristic of the basic structure of most of the polyunsaturated fatty acid metabolites.In this paper are described our results concerning a new approach towards molecules of this type.The key features of this strategy include: 1) the use of the, easily available, fumaraldehyde monodimethylacetal 4 as a key intermediate for the synthesis of such compounds in racemic form and 2) the use of the chiral sorbic acid tricarbonyl ion complex 8 as a resolving agent.The methodology allows then the synthesis of several fatty acid metabolites such as 4-hydroxy-2-nonenal 14, coriolic and tetranorcoriolic acid methyl esters 28 and 31, trienals 39 or 40, and the 12-hydroxy-5,8,10 heptadecatrienoic ester 41.Some of them have been tested as part of a program dealing with the interaction of blood platelets and eicosanoids; it gave new results concerning the influence of the absolute configuration at the carbon bearing the hydroxyl group and the stereochemistry of the diene.