7149-92-0

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dimethoxy-3-methylbenzaldehyde is used as a starting reagent in the stereo-controlled total synthesis of (+)-kendomycin, a potent antibiotic with broad-spectrum activity against both Gram-positive and Gram-negative bacteria. Its unique structure allows for the development of new and effective treatments for bacterial infections.
Additionally, 2,4-Dimethoxy-3-methylbenzaldehyde is used as a starting reagent in the total syntheses of renierol, renierol acetate, and renierol propionate. These compounds have potential applications in the development of new pharmaceuticals and therapeutic agents, further highlighting the importance of 2,4-Dimethoxy-3-methylbenzaldehyde in the pharmaceutical industry.

InChI:InChI=1/C10H12O3/c1-7-9(12-2)5-4-8(6-11)10(7)13-3/h4-6H,1-3H3

Upstream product

• 5673-07-4 2,6-dimethoxytoluene 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 4885-02-3 Dichloromethyl methyl ether 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 74-88-4 methyl iodide 
• 6248-20-0 2,4-dihydroxy-3-methylbenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 107-30-2 chloromethyl methyl ether 
• 608-25-3 2-methylbenzene-1,3-diol 

Downstream Products

• 82622-02-4 5-(benzyloxy)-2,4-dimethoxy-3-methylbenzaldehyde 
• 19676-67-6 2,4-dimethoxy-3-methylphenol 
• 24160-27-8 2-(2,4-Dimethoxy-3-methyl-phenyl)-1-methyl-ethylamine 
• 685895-46-9 acetic acid acetoxy-(2,4-dimethoxy-3-methyl-5-nitro-phenyl)-methyl ester 
• 22304-73-0 5-Chlormethyl-2,4-dimethoxy-3-methyl-benzaldehyd 
• 771586-41-5 (S)-2-{[(S)-tert-Butylcarbamoyl-(2,4-dimethoxy-3-methyl-phenyl)-methyl]-amino}-pentanedioic acid dimethyl ester 
• 853995-97-8 2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde 

Relevant academic research and scientific papers

Azaphilones as Activation-Free Primary-Amine-Specific Bioconjugation Reagents for Peptides, Proteins and Lipids

Residue-selective bioconjugation methods for biomolecules are highly sought to expand the scope of their biological and medical applications. Inspired by the mechanism of the generation of natural vinylogous γ-pyridones (vPDNs), we have developed a novel

Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control

A stereogenic center, placed at an exocyclic location next to a chiral carbon in a ring to which it is attached, is a ubiquitous structural motif seen in many bioactive natural products, including di- and triterpenes and steroids. Installation of these ce

Enantioselective Synthesis of (+)-Mitomycin K by a Palladium-Catalyzed Oxidative Tandem Cyclization

The mitomycins, a family of bioactive natural products, feature a compact 6/5/5-fused polycyclic ring structure densely decorated with highly reactive and/or fragile quinone, amino ketal, and aziridine as well as carbamate moieties. It is this striking feature that has defeated numerous synthetic attempts towards these apparently small molecules, rendering them one of the most formidable targets for total synthesis. We herein report the first enantioselective synthesis of (+)-mitomycin K, a representative of G series mitomycins. The key step of this synthesis is an enantioselective oxidative cyclization catalyzed by a palladium/(+)-sparteine system that had previously been developed by our group. The robustness of this method bodes well for further applications in the asymmetric total synthesis of natural products, particularly those with characteristic 6/5/5-fused pyrroloindole skeletons.

Synthesis of a leucomitosane via a diastereoselective radical cascade

The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones

Total synthesis of (-)-lemonomycin

When life gives you lemons: An efficient and convergent enantioselective total synthesis of (-)-lemonomycin, which shows potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF), is presented. The key reaction steps are a Hosomi-Sakurai-type cyclization, a thermodynamically controlled Pictet-Spengler reaction, and a glycosidation reaction with lemonose (see scheme). Copyright

Synthetic studies on (-)-lemonomycin: An efficient asymmetric synthesis of lemonomycinone amide

Asymmetric synthesis of lemonomycinone amide (2) was accomplished from readily accessible starting materials. Enantioselective alkylation of N-(diphenylmethylene)glycine tert-butyl ester (11) by 5-tert- butyldimethylsilyloxy-2,4-dimethoxy-3-methylbenzyl bromide (10) in the presence of Corey-Lygo's phase transfer catalyst [O-(9)-ally-N-(9-anthracenylmethyl) cinchonidium bromide, 0.1 equiv] afforded, after chemoselective hydrolysis of the imine function (THF/H2O/AcOH), the substituted L-tert-butyl phenylalanate 13 in 85% yield. A Pictet-Spengler reaction of 14 with benzyloxyacetaldehyde (15) provided the 1,3-cisdisubstituted tetrahydroisoquinoline 16 in 85% yield as a single diastereomer. Coupling of hindered secondary amine 16 with amino acid 9 was accomplished under carefully controlled conditions to furnish the amide 22, which was in turn converted to hemiaminal 24. A hafnium triflate catalyzed conversion of hemiaminal to α-amino thioether followed by a silver tetrafluoroborate promoted intramolecular Mannich reaction of 26 afforded the tetracycle 27 in excellent overall yields. Debenzylation of 27 [Pd(OH)2, H2, MeOH, 0°C], removal of N-Boc function (aqueous 3 N HCl, MeOH/H2O), and oxidation of hydroquinone to quinone [(NH4)2Ce(NO 3)6, H2O, rt] afforded the lemonomycinone amide 2 in 76% yield over three steps

Asymmetrie total syntheses of (-)-renieramycin M and G and (-)-jorumycin using aziridine as a lynchpin

"Chemical Equation Presented" By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.

New Drug Delivery System for Crossing the Blood Brain Barrier

New ubiquinol analogs are disclosed, as well as methods of using these compounds to deliver drug moieties to the body.

Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy

A convergent stereocontrolled total synthesis of (-)-kendomycin (1) has been achieved. The synthesis proceeds with a longest linear sequence of 21 steps, beginning with commercially available 2,4-dimethoxy-3-methylbenzaldehyde (12). Highlights of the synthesis include an effective Petasis-Ferrier union/rearrangement tactic to construct the sterically encumbered tetrahydropyran ring, a ring-closing metathesis to generate the C(4a-13-20a) macrocycle, an effective epoxidation/deoxygenation sequence to isomerize the C(13,14) olefin, and a biomimetic quinone-methide-lactol assembly to complete the synthesis.

Rapid stereocontrolled assembly of the fully substituted C-aryl glycoside of kendomycin with a Prins cyclization: A formal synthesis

Prins cyclization using an electron-rich benzaldehyde and a homoallylic alcohol efficiently delivered the fully substituted C-aryl tetrahydropyranoside of kendomycin. The Royal Society of Chemistry 2006.