37384-77-3

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 79-77-6 (E)-β-ionone 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 884845-78-7 N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide 
• 42520-11-6 1,1-diethoxy-2-bromo-ethene 

Downstream Products

• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 3917-40-6 (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienol 
• 14398-42-6 (2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoic acid 
• 49817-16-5 β-apo-12-carotenol 
• 5560-99-6 (2X,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienal 
• 49817-06-3 ethyl (4E)-3-methyl-5-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienoate 

Relevant academic research and scientific papers

Obtention of 2,2-(diethoxy) vinyl lithium and 2-methyl-4-ethoxy butadienyl lithium by Arene-catalysed lithiation of the corresponding chloro derivatives. Synthetic applications

Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal 13 from β-cyclocitral 10.

Chiral Amplification in Nature: Studying Cell-Extracted Chiral Carotenoid Microcrystals via the Resonance Raman Optical Activity of Model Systems

Carotenoid microcrystals, extracted from cells of carrot roots and consisting of 95 % of achiral β-carotene, exhibit a very intense chiroptical (ECD and ROA) signal. The preferential chirality of crystalline aggregates that consist mostly of achiral building blocks is a newly observed phenomenon in nature, and may be related to asymmetric information transfer from the chiral seeds (small amount of α-carotene or lutein) present in carrot cells. To confirm this hypothesis, we synthesized several model aggregates from various achiral and chiral carotenoids. Because of the sergeant-and-soldier behavior, a small number of chiral sergeants (α-carotene or astaxanthin) force the achiral soldier molecules (β- or 11,11′-[D2]-β-carotene) to jointly form supramolecular assemblies of induced chirality. The chiral amplification observed in these model systems confirmed that chiral microcrystals appearing in nature might consist predominantly of achiral building blocks and their supramolecular chirality might result from the co-crystallization of chiral and achiral analogues.

Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins

Three all-trans retinals containing multiple 13C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsi

Accurate measurements of 13C-13C J-couplings in the rhodopsin chromophore by double-quantum solid-state NMR spectroscopy

A new double-quantum solid-state NMR pulse sequence is presented and used to measure one-bond 13C-13C J-couplings in a set of 13C2-labeled rhodopsin isotopomers. The measured J-couplings reveal a perturbation of the electronic structure at the terminus of the conjugated chain but show no evidence for protein-induced electronic perturbation near the C11-C12 isomerization site. This work establishes NMR methodology for measuring accurate 1JCC values in noncrystalline macromolecules and shows that the measured J-couplings may reveal local electronic perturbations of mechanistic significance. Copyright

Microwave Accelerated Wittig Reactions of Stabilized Phosphorus Ylides with Ketones under Solvent-Free Conditions

Microwave irradiation accelerates some difficult Wittig reactions of stable phosphorus ylides (e.g. 1) with ketones. Irradiation in a domestic microwave oven of the mixture of reactants, in absence of solvents, allowed to obtain, in shorter times, an impr

2,2-Di(ethoxy)vinyllithium: Reactions with carbonyl compounds

2,2-Di(ethoxy)vinyllithium 2 generated from bromo ketene acetal 1 reacts with carbonyl compounds to give either β-hydroxy esters 5 or conjugated esters 6 or hydroxy ketene acetals 7 according to the work up.

THE APPLICATION OF HIGH PRESSURE TO SOME DIFFICULT WITTIG REACTIONS

Wittig reactions, previously shown to be favourably accelerated under pressure have been carried out between the stabilized ylides carboethoxymethylenetriphenylphosphorane and carboethoxyethylidinetriphenylphosphorane with a variety of ketones at 9-10 kbar pressure.Succesful formation of tri- and tetra-substituted ethylenes are reported.

Total Synthesis of 3,4,3',4'-Tetradehydro-β,β-carotene-2,2'-dione

The first total synthesis of 3,4,3',4'-tetradehydro-β,β-carotene-2,2'-dione is reported, confirming the structure previously assigned to a carotenoid isolated from stick insects (Plasmida).Conversion of the corresponding bisallylic diol to the aromatic is