74422-90-5

Upstream product

• 93-02-7 2,5-dimethoxybenzaldehyde 
• 34549-69-4 3-nitro-5-methoxysalicylaldehyde 
• 77-78-1 dimethyl sulfate 
• 7697-37-2 nitric acid 
• 85432-87-7 2-bromo-3,6-dimethoxybenzaldehyde 
• 74-88-4 methyl iodide 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 74422-83-6 2,5-dimethoxy-3,β-dinitrostyrene 
• 134333-56-5 (2S,5S,6R)-(E)-methyl 6-(2,5-dimethoxy-3-nitrophenyl)-2,6-dimethoxy-5-methylhex-3-enoate 
• 115820-52-5 (4R,5S)-3-<(2R,3R)-3-(2,5-Dimethoxy-3-nitrophenyl)-3-hydroxy-2-methylpropanoyl>-4-methyl-5-phenyl-2-oxazolidinone 
• 115889-49-1 (4R,5S)-3-[(2R,3S)-3-(2,5-Dimethoxy-3-nitro-phenyl)-3-hydroxy-2-methyl-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 115889-48-0 (4R,5S)-3-[(2S,3S)-3-(2,5-Dimethoxy-3-nitro-phenyl)-3-hydroxy-2-methyl-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 115889-47-9 (4R,5S)-3-[(2S,3R)-3-(2,5-Dimethoxy-3-nitro-phenyl)-3-hydroxy-2-methyl-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 161926-56-3 3-[1,3]Dithian-2-yl-2,5-dimethoxy-phenylamine 
• 206555-19-3 2-(2,5-Dimethoxy-3-nitro-phenyl)-[1,3]dithiane 
• 198758-06-4 (2,5-dimethoxy-3-nitrophenyl)methanol 
• 17894-26-7 2,5-dimethoxy-3-nitro-benzoic acid 
• 408535-54-6 (2,5-dimethoxy-3-nitro)-benzaldehyde dithiophenylacetal 
• 1259234-75-7 (R)-4-benzyl-3-((4R,5S,E)-5-(2,5-dimethoxy-3-nitrophenyl)-5-hydroxy-2,4-dimethylpent-2-enoyl)oxazolidin-2-one 
• 1259234-51-9 (S)-4-benzyl-3-((4S,5R,E)-5-(2,5-dimethoxy-3-nitrophenyl)-5-hydroxy-2,4-dimethylpent-2-enoyl)oxazolidin-2-one 
• 34549-69-4 3-nitro-5-methoxysalicylaldehyde 

Relevant academic research and scientific papers

Total Synthesis and Structural Revision of Clavilactone D

A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.

Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS)

A reliable and accurate GC-MS method was developed that allows both mass spectrometric and chromatographic discrimination of the six aromatic positional isomers of trimethoxyamphetamine (TMA). Regardless of the trifluoroacetyl (TFA) derivatization, chromatographic separation of all the investigated isomers was achieved by using DB-5ms capillary columns (30 m x 0.32 mm i.d.), with run times less than 15 min. However, the mass spectra of the nonderivatized TMAs, except 2,4,6-trimethoxyamphetmine (TMA-6), showed insufficient difference for unambiguous discrimination. On the other hand, the mass spectra of the TFA derivatives of the six isomers exhibited fragments with significant intensity differences, which allowed the unequivocal identification of all the aromatic positional isomers investigated in the present study. This GC-MS technique in combination with TFA derivatization, therefore, is a powerful method to discriminate these isomers, especially useful to distinguish the currently controlled 3,4,5-trimethoxyamphetmine (TMA-1) and 2,4,5-trimethoxyamphetmine (TMA-2) from other uncontrolled TMAs. Copyright

A practical synthesis of the ansa chain of benzenic ansamycin antibiotics: Total synthesis of an ansatrienol derivative

A practical and stereocontrolled synthetic approach towards the ansa chain of the benzenic ansamycins (mycotrienins) is described, which can be scaled up to multigram quantities. Key features of the synthesis are the formation of the Z-configured tri-subs

Re-examination of the synthesis of 3,5-dimethoxy-2-nitrobenzaldehyde

An efficient and reproducible synthetic method is proposed for the preparation of 2-nitro-3,6-dimethoxybenzaldehyde.

Total Synthesis of (+)-Macbecin I

The first total enantiospecific synthesis of (+)-macbecin I has been performed in a convergent manner by coupling the epoxide (3) with a higher order cyanocuprate derived from the vinyl iodide (46).The required absolute stereochemistries at C(20)-C(21) and C(12)-C(13) were accessible by enantioselective aldol condensations while that at C(16)-C(17) was achieved by Sharpless epoxidation of a secondary (E)-allylic alcohol (39), efficiently prepared by reaction of the aldehyde (37) with CrCl2-CH3CHI2.The remaining stereocentre at C-18 was introduced by an asymmetric hydroxylation of an enolate.Macrocyclization of the amino acid (59) to give the lactam (60) was successfully achieved by its reaction with either 2-mesitylenesulphonyl chloride or bis(2-oxo-3-oxazolidinyl)phosphinic chloride.Incorporation of the carbamate functionality was achieved by reaction of the parent hydroxy derivative with sodium cyanate and trifluoroacetic acid.The final oxidation to the quinone was accomplished with cerium(IV) ammonium nitrate.

Light Absorption and Emission Properties of Cyanovinyl-substituted Dimethoxybenzenes

Synthetic routes to a range of dyes based on cyanovinyl-substituted dimethoxybenzenes are described.The light absorption and fluorescence properties of these compounds in fluid solution at room temperature are discussed.