61898-56-4

Upstream product

• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 68702-74-9 methyl 3-(R)-methyl-5-hydroxypentanoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 83588-21-0 5-Methoxymethoxy-3-methyl-pentanoic acid 
• 2381-87-5 4-methyl-5,6-dihydro-2H-pyran-2-one 
• 3393-45-1 5,6-dihydro-pyran-2-one 
• 544-97-8 dimethyl zinc(II) 
• 4166-53-4 3-methylglutaric anhydride 
• 72594-19-5 (R)-1-ethyl hydrogen-3-methylglutarate 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 1360067-14-6 C₁₄H₁₉NO 
• 80039-52-7 acrylic acid 3-methyl-but-3-enyl ester 
• 91794-29-5 3(S)-methyl-5-oxo-5-(1-piperidyl)pentan-1-ol 
• 107442-11-5 (S)-5-Hydroxy-3-methyl-pentanoic acid phenylamide 

Downstream Products

• 234447-83-7 (3S)-5-hydroxy-N-(4-methoxybenzyl)-3-methylpentanamide 
• 234447-85-9 (4R)-1-(4-methoxybenzyl)-4-methyl-3,4-dihydropyridin-2-one 
• 234447-84-8 (4S)-6-hydroxy-1-(4-methoxybenzyl)-4-methylpiperidin-2-one 
• 586398-87-0 (1S,5R,6R)-7-bromo-7-fluoro-2-(4-methoxybenzyl)-5-methyl-2-azabicyclo[4.1.0]heptan-3-one 
• 586398-80-3 (1R,5R,6S)-7-bromo-7-chloro-2-(4-methoxybenzyl)-5-methyl-2-azabicyclo[4.1.0]heptan-3-one 
• 586398-86-9 (1S,5R,6R)-7-bromo-7-chloro-2-(4-methoxybenzyl)-5-methyl-2-azabicyclo[4.1.0]heptan-3-one 
• 586398-78-9 (1R,5R,6S)-7,7-dichloro-2-(4-methoxybenzyl)-5-methyl-2-azabicyclo[4.1.0]heptan-3-one 
• 1352757-71-1 C₂₆H₃₈O₄Si 
• 1352757-92-6 C₂₇H₄₀O₄Si 
• 1352757-93-7 C₂₉H₄₄O₅Si 
• 63314-79-4 (3R,5Z)-3-methylcyclopentadec-5-enone 
• 68274-97-5 dec-5-yn-1-ol 
• 82538-58-7 (3R)-5-(benzyloxy)-3-methylpentanal 

Relevant academic research and scientific papers

Consturuction of a complete bioelectrocatalytic electrode composed of alcohol dehydrogenase-and all electron-transfer components-modified graphite felt for diol oxidation

A poly(acrylic acid)-coated graphite felt electrode immobilizing all bioelectrochemical reaction components of ferrocene, diaphorase, NADH and alcohol dehydrogenase in the domain of the poly(acrylic acid) layer was applied to oxidize electrocatalytically cis-1,2-cyclohexanedimethanol and 3-methyl-1,5-pentanediol to (+)-(1R,6S)-cis-8-oxabicyclo[4.3.0]nonan-7-one and (3S)-3-methyl-δ-valerolactone, respectively, in a 0.15 M phosphate buffer (pH 8.0) at the constant potential of 0.45 V vs. SCE with high current efficiency (>92%) and high optical purity (>92%).

An efficient route to the musk odorant (R,Z)-5-muscenone via base-metal-catalysis

Muscenone is a valuable perfume ingredient consisting of a mixture of the E- and Z-isomers of 1 in racemic form as the major constituents. Among them, it is the (R,Z)-isomer, which exhibits the most favorable musk character and by far the lowest threshold; for these superior olfactory properties, pure (R,Z)-1 has recently been commercialized too. We present an efficient route to this precious compound based on an iron-catalyzed cross coupling reaction, a molybdenum-catalyzed alkyne metathesis for the formation of the macrocyclic ring, and a nickel-catalyzed semi-hydrogenation.

Photobiocatalytic alcohol oxidation using LED light sources

The photocatalytic oxidation of NADH using a flavin photocatalyst and a simple blue LED light source is reported. This in situ NAD+ regeneration system can be used to promote biocatalytic, enantioselective oxidation reactions. Compared to the traditional use of white light bulbs this method enables very significant reductions in energy consumption and CO2 emission.

Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen

The application of synthetic flavinium organocatalysts for the in situ regeneration of oxidized cofactors NAD(P)+ using O2 as the terminal oxidant without any special illumination or equipment is reported. With the aid of the highly active bridged flavinium catalyst, the rate of NAD(P)H oxidation is accelerated by 3 orders of magnitude. The results show that the catalytic activity of the bridged flavinium catalyst is not dependent on light but on only oxygen. Furthermore, this catalyst is compatible with various preparative enzymatic oxidation reactions. A hydride transfer mechanism is proposed for the presented system.

Desymmetrization of acid anhydride with asymmetric esterification catalyzed by chiral phosphoric acid

Asymmetric desymmetrization of σ-symmetric acid anhydrides was achieved with chiral phosphoric acid as a Br?nsted acid catalyst. The key of success was finding of benzhydrol and 2,2-diphenylethanol as the nucleophiles of choice. The corresponding half esters were obtained in good yields with high selectivity.

Biocatalytic Characterization of Human FMO5: Unearthing Baeyer-Villiger Reactions in Humans

Flavin-containing mono-oxygenases are known as potent drug-metabolizing enzymes, providing complementary functions to the well-investigated cytochrome P450 mono-oxygenases. While human FMO isoforms are typically involved in the oxidation of soft nucleophiles, the biocatalytic activity of human FMO5 (along its physiological role) has long remained unexplored. In this study, we demonstrate the atypical in vitro activity of human FMO5 as a Baeyer-Villiger mono-oxygenase on a broad range of substrates, revealing the first example to date of a human protein catalyzing such reactions. The isolated and purified protein was active on diverse carbonyl compounds, whereas soft nucleophiles were mostly non- or poorly reactive. The absence of the typical characteristic sequence motifs sets human FMO5 apart from all characterized Baeyer-Villiger mono-oxygenases so far. These findings open new perspectives in human oxidative metabolism.

A new method for the preparation of non-terminal alkynes: Application to the total syntheses of tulearin A and C

Lactones are known to react with the reagent generated in situ from CCl4 and PPh3 in a Wittig-type fashion to give gem-dichloro-olefin derivatives. Such compounds are now shown to undergo reductive alkylation on treatment with organolithium reagents RLi to furnish acetylene derivatives bearing the substituent R at their termini (R=Me, n-, sec-, tert-alkyl, silyl); the reaction can be catalyzed with either Cu(acac)2 or Fe(acac)3/1,2-diaminobenzene. Two alkynol derivatives prepared in this way from readily accessible lactone precursors served as the key building blocks for the total syntheses of the cytotoxic marine macrolides tulearin A (1) and C (2). The assembly of these fragile targets hinged upon ring closing alkyne metathesis (RCAM) followed by a formal trans-reduction of the resulting cycloalkynes via trans-hydrosilylation/protodesilylation.

Stereoselective synthesis of two highly potent 5-oxo-ETE receptor antagonists

Enantioselective synthesis of highly potent 5-oxo-ETE receptor antagonists 5a and 6a with a high level of enantiomeric purity is described. The main feature of this work is the simple and efficient synthesis of the bi-functionalized 3-(S)-methyl-pentanedi

Cyclopropanol Methodology in the Synthesis of (4R)- and (4S)-4-Methyltetrahydro-2H-pyran-2-ones. Application in the Synthesis of Insect Pheromones with Methyl-Branched Carbon Skeleton

A number of chiral methyl-branched building blocks have been synthesized starting from (4S)-4-methyltetrahydro-2H-pyran-2-one, and the possibility for using them for the preparation of mealworm beetle, rhinoceros beetle, and earth-boring dung beetle phero

Access to lactone building blocks via horse liver alcohol dehydrogenase-catalyzed oxidative lactonization

The oxidative lactonization of 1,4-, 1,5-, and 1,6-diols using horse liver alcohol dehydrogenase (HLADH) is reported. Molecular oxygen was used as terminal electron acceptor by utilization of the laccase-mediator concept to regenerate the oxidized nicotinamide cofactor and producing water as sole byproduct. Spontaneous hydrolysis of the lactone products was identified as a major limiting factor toward preparative application of the system, which can be alleviated by using a two liquid phase approach to extracting the product into an organic solvent.