54340-91-9

Upstream product

• 106-73-0 methyl heptanoate 
• 186581-53-3 diazomethane 
• 52358-05-1 2-hydroxyheptanoic acid 
• 86593-94-4 (E/Z)-1-methoxy-1-trimethylsilyloxy-1-heptene 
• 81114-75-2 1,1,1-tris(methylthio)-2-heptanol 
• 78935-59-8 E-methoxy-1 trimethylsiloxy-1 heptene-1 
• 74-88-4 methyl iodide 
• 145090-37-5 Acetic acid 1-methylsulfanylcarbonyl-hexyl ester 
• 66-25-1 hexanal 
• 67-56-1 methanol 
• 82722-11-0 1,1,1-Tris-ethylsulfanyl-heptan-2-ol 
• 2863-47-0 1-methanesulfinyl-heptan-2-one 
• 106-70-7 methyl hexanoate 

Downstream Products

• 56196-51-1 α-Acetoxy-heptansaeure-methylester 
• 54004-30-7 (E)-methyl hept-3-enoate 

Relevant academic research and scientific papers

Oxidation of Methyl Trimethylsilyl Ketene Acetals to α-Hydroxyesters with Urea Hydrogen Peroxide Catalyzed by Methyltrioxorhenium

In the presence of catalytic amounts of MTO, methyltrioxorhenium, methyl trimethylsilyl ketene acetals are oxidized with urea hydrogen peroxide to afford α-hydroxy and α-siloxy esters. On treatment with potassium fluoride, the α-hydroxy esters are obtained in high yields.

An efficient α-hydroxylation of carbonyls using the HOF·CH3CN complex

The complex HOF·CH3CN, made directly from fluorine and aqueous acetonitrile, was used for α-hydroxylation of various ketones, esters and acids via their trimethyl silyl enol ethers. The reaction is usually complete in a few minutes at room temperature or below and has high yields.

4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5- analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis

A stereoselective synthesis of the lipid peroxidation products 4- hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)- catalyzed oxidative degradation and subsequent stereoanalysis of the resulting α-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.

A convenient route for the homologation of saturated esters to α,β-unsaturated esters

Methyl hexanoate (1a) is transformed to methyl 2-hydroxyheptanoate (5a) employing the following sequence of reactions (Scheme 1); (i) reaction with sodium hydride-dimethyl sulfoxide, (ii) Pummerer rearrangement with acetic anhydride-sodium acetate, (iii) alkaline hydrolysis and (iv) esterification with diazomethane.The α-hydroxy ester (5a) is converted into methyl 2E-heptenoate (7a) employing the following reactions (Scheme 2); (i) reaction with phosphorous tribromide and (ii) elimination using DBU.Thus, the sequence of reactions given in Schemes 1 and 2 provide aconvenient route for the one carbon homologation of saturated esters to α,β-unsaturated esters.

Synthesis of S-Methyl 2-Hydrxyalkanethioates, 2-Hydroxyalkanoic Acids and Related Compounds via the Addition Reaction of Tris(methylthio)methanide Ion to Alkanals

In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied.The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal-dodecanal) gave the corresponding 1,1,-tris(methylthio)-2-alkanols 1a-j.Treatment of 1 with mercury(II) chloride-mercury(II) oxide in water-acetone afforded S-methyl 2-hydroxyalkanethioates 2a-j, and in methanol methyl 2-hydroxyalkanoates 3c-j were obtained.Reduction of the thioates 2 with lithium aluminium hydride gave 1,2-diols 4c-j and saponification produced the corresponding 2-hydroxyalkanoic acids 5c-j.