27167-79-9

Upstream product

• 27159-99-5 4-hydroxy(²H₂)methyl-1,2-dimethoxybenzene 
• 50766-67-1 2-(3,4-dimethoxyphenyl)-1,3-dithiane 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 93-07-2 Veratric acid 
• 379692-55-4 (R)-[α-2H1]veratryl alcohol 
• 379692-57-6 (S)-[α-2H1]veratryl alcohol 
• 106053-24-1 2-deutero-2-(3,4-dimethoxyphenyl)-1,3-dithiane 

Downstream Products

• 1158815-29-2 C₂₁H₂₁⁽²⁾HN₂O₄*ClH 
• 106053-32-1 cis-α,α'-Dideutero-3,4,4'-trimethoxystilben 
• 106053-31-0 trans-α,α'-Dideutero-3,4,4'-trimethoxystilben 
• 106053-28-5 cis-α-Deutero-3,4,4'-trimethoxystilben 
• 106053-27-4 trans-α-Deutero-3,4,4'-trimethoxystilben 

Relevant academic research and scientific papers

Selective oxidation of alcohol-d1to aldehyde-d1using MnO2

The selective oxidation of alcohol-d1to prepare aldehyde-d1was newly developed by means of NaBD4reduction/activated MnO2oxidation. Various aldehyde-d1derivatives including aromatic and unsaturated ald

Differences in the Mechanisms of MnO2Oxidation between Lignin Model Compounds with the p-Hydroxyphenyl, Guaiacyl, and Syringyl Nuclei

The purpose of this study was to examine how the rate and mechanism of MnO2 oxidation differ between the p-hydroxyphenyl (H), guaiacyl (G), and syringyl (S) types of simple nonphenolic lignin model compounds as well as the p-ethylphenyl (E) type compounds. The oxidation was conducted using an excess amount of MnO2 in a sulfate buffer solution at a pH value of 1.5 at room temperature. MnO2 oxidized at least the G and S nuclei, although it commonly oxidizes alcohols present at the benzyl position. The oxidation rates of the benzyl alcohol derivatives were in the order of G- > S- ? H- > E-type, which suggests that the rates are determined by the electronic effects of their methoxy and ethyl functional groups on not only their benzyl positions but also their aromatic π-electron systems. The kinetic isotope effect was observed in the MnO2 oxidations of the same derivatives deuterated at their benzyl hydroxymethyl groups. The observed magnitudes were in the order of E- ? H- > G- ? S-type, suggesting that the contribution of oxidation of their aromatic nuclei, which is another reaction mode of the oxidation of their benzyl positions, increases in the reverse order.

Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: highly stereoselective Pictet-Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes

A highly stereoselective Pictet-Spengler reaction of d-tryptophan methyl ester hydrochloride 1-HCl with various aldehydes via a CIAT (crystallization-induced asymmetric transformation) process is described. It was revealed that the CIAT process should be

Kinetic deuterium isotope effect in the oxidation of veratryl alcohol promoted by lignin peroxidase and chemical oxidants

The intramolecular kinetic deuterium isotope effects (kH/kD = 4.6-4.9) determined in the H2O2-induced oxidation of the racemic and enantiomeric forms of α-monodeuterated veratryl alcohol catalysed by lignin peroxidase (LiP) are very similar to those determined in the oxidation of racemic α-monodeuterated veratryl alcohol promoted either by a LiP model compound (a water soluble iron porphyrin using m-chloroperbenzoic acid as the oxidant) (kH/kD = 4.2) or by potassium 12-tungstocobalt(III)ate, a genuine one-electron oxidant (kH/kD = 4.5). These results indicate that very likely veratryl alcohol radical cation, once generated by the LiP-H2O2 system, is released from the enzyme and is deprotonated by the medium.

Stereochemical control in microbial reduction. XXVIII. Asymmetric reduction of α,β-unsaturated ketones with Bakers' yeast

Bakers' yeast reduction of α,β-unsaturated ketones affords optically active saturated ketones contaminated by allylic and saturated alcohols as minor components. Stereoselectivity of the reduction of carbon-carbon double bond strongly depends on the structure of β-aryl substituent. The bakers' yeast reduction of β-phenyl enones gives saturated ketones in moderate stereoselectivity. Stereoselectivity is not altered by substitution at the para-position, whereas introduction of a substituent at the ortho- or meta-position drastically improves the stereoselectivity. Deuterium-labeling experiments reveal that the enzymatic reduction of carbon-carbon double bond proceeds with formal trans-addition of hydrogens regardless the efficiency of stereoselectivity. The resulting optically active ketone was converted to the precursor of (S)-iopanoic acid, an inhibitor of thyroxine 5′-deiodinase that is a thyroid hormone-converting enzyme and an oral cholecystographic agent.

Syntheses og Stilbenes with a C2-Sidechain in o-Position and of their Deuteriated Analogues

Syntheses of o-(β-aminoethyl)-stilbene-urethanes (types 1, 2 and 3) and o-(β-phenethyl)-stilbenes 4 are described.The urethanes are obtained by degradation of 1-benzyl-1,2,3,4-tetrahydroisoquinolines with ethylchloroformate; 4 is synthesized by reduction of desoxybenzoines, followed by o-formylation and Wittig-reaction.The deuteriated isotopomers were obtained via the corresponding deuteriated precursors. - Keywords: Stilbenes, o-substituted; Deuteriated compounds

BIOMIMETIC OXIDATIONS OF BENZYLISOQUINOLINE ALKALOUDS. II. THE BIS(SALICYLALDEHYDE)ETHYLENEDIIMINECOBALT(II)-CATALYZED OXIDATION OF BENZYLISOQUINOLINES WITH OXYGEN

The complex bis(salicylaldehyde)ethylenediiminecobalt(II) (CoII salen) catalyzes the oxidation of benzylisoquinoline alkaloids with oxygen.Aminium radicals are formed and give rise to 1,2-dehydrobenzylisoquinoline ions.Cleavage of the C(1)-C(9) bond via C(9) oxidation is observed in some instances.