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• 592-02-9 diethylcadmium 
• 543-20-4 succinoyl dichloride 
• 1113-00-4 4-ethyl-hexane-1,4-diol 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 84786-96-9 1-(2-chloroethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 
• 96-22-0 pentan-3-one 
• 108-30-5 succinic acid anhydride 
• 925-90-6 ethylmagnesium bromide 
• 584-02-1 2-pentanol 
• 292638-85-8 acrylic acid methyl ester 
• 74-96-4 ethyl bromide 
• 121802-58-2 (Z)-3-Ethyl-6-(1-methoxymethyl-1H-imidazol-2-yl)-6-triisopropylsilanyloxy-hex-5-en-3-ol 
• 107-94-8 chloropropionic acid 

Relevant academic research and scientific papers

Bifunctional Even-electron Ions III. Fragmentation Behaviour of aliphatic Hydroxonium Ions Containing an Additional Carbomethoxy Group

The primary and subsequent fragmentaations of the bifunctional oxonium ions R-C+(OH)-(CH2)n-COOCH3 (n = 0-5), a, are dominated by functional group interactions.Loss of CH3OH os the only appreciable primary fragmentation of the higher homologues, but for the lowest homologue (a0) this reaction is missing.Instead, CO loss is observed.The next homologue (a1) shows loss of CH2CO besides loss of CH3OH.The mode of the subsequent fragmentations is dependent on the chain length separating the functional group, and formation of cyclic ions is typical of the fragmentation behaviour of a2 and a3.Evidence for proton transfer from the carbonyl oxygen to the methoxy group of a protonated ester group is presented.

Scalable synthetic oligodeoxynucleotide purification with use of a catching by polymerization, washing, and releasing approach

Synthetic oligodeoxynucleotides are purified with use of a catching by polymerization, washing, and releasing approach. The method does not require any chromatography, and purification is achieved by simple operations such as shaking, washing, and extraction. It is therefore useful for large-scale purification of synthetic oligonucleotide drugs. In addition to purification of oligonucleotides, this catching by polymerization concept is expected to be equally useful for purification of other synthetic oligomers such as peptides and oligosaccharides.

O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols

The efficiency and selectivity of hydrogen atom transfer from organic molecules are often difficult to control in the presence of multiple potential hydrogen atom donors and acceptors. Here, we describe the mechanistic evaluation of a mode of catalytic activation that accomplishes the highly selective photoredox a-alkylation/lactonization of alcohols with methyl acrylate via a hydrogen atom transfer mechanism. Our studies indicate a particular role of tetra-n-butylammonium phosphate in enhancing the selectivity for α C-H bonds in alcohols in the presence of allylic, benzylic, α-C=O, and α-ether C-H bonds.

A novel synthesis of γ,δ-unsaturated aldehydes from α-formyl-γ-lactones

A preparatively useful one-step transformation of γ,γ- disubstituted α-formyl-γ-lactones into trisubstituted γ,δ-unsaturated aldehydes is described, by means of catalytic amounts of either AcOH or AcOEt in the vapor phase over a glass support. A mechanistic rationale is proposed. Copyright

Structural and stereochemical requirements of the spiroketal group of hippuristanol for antiproliferative activity

Hippuristanol is a natural product that has recently been shown to inhibit eukaryotic translation initiation and tumor cell proliferation. To investigate the structure and activity relationship of hippuristanol, we synthesized a series of analogs by expan

Masked ω-lithio ester enolates: Synthetic applications

The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4'-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ortho esters 14: the β-chloro OBO ester derivate generates the γ-lactones 15 and the γ-chloro OBO ester gives corresponding esters 8.

Synthesis of new furan derivatives and 4-hydroxy aldehydes from 4-hydroxy 1-enol ethers

Starting from 4-hydroxy 1-enol ethers 3 different γ-lactols 4 were successfully prepared by acidic hydrolysis. Subsequent oxidation of 4 with pyridinium chlorochromate (PCC) led to γ-lactones 6 in good to excellent overall yields. Treatment of γ-lactols 4

Masked β-, γ- and δ-lithium ester enolates: Useful reagents in organic synthesis

The reaction of ω-chloro orthoesters 1 with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in the presence of different electrophiles [ButCHO, PhCHO, (CH2)5CO, Et2CO, PhCOMe, PhCH=NPh, Me3SiCl] in THF at -78°C leads, after hydrolysis and acid-catalysed methanolysis, to functionalised methyl esters 2. In the case of chlorotrimethylsilane, hydroxyethyl esters 2′ are isolated. The reaction is also applied to bicyclic orthoesters 3: whereas β-chloro derivatives and carbonyl compounds gives directly γ-lactones 4 after hydrolysis, the corresponding γ-chloro derivative affords the expected methyl esters after methanolysis.

Lithium- α-lithioacetate and β-lithiopropionate: Useful intermediates in organic synthesis

The reaction of chloroacetic acid and 3-chloropropionic acid with a base (LDA or Bu(n)Li, respectively) and then with an excess of lithium and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 5%) in the presence of different electrophiles [Bu'CHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe] in THF at -78°C leads, after hydrolysis with water, to the expected hydroxy acids, which in the second case are directly cyclised under acidic conditions to give the expected γ-lactones. (C) 2000 Elsevier Science Ltd.

Synthesis of γ-Lactones from intermediate 2-(γ-Hydroxyacyl)imidazoles by N-Methylation and Base-catalyzed C-C Bond Cleavage. Application to the Synthesis of (+/-)-Cavernosin

Reaction of the allyl anions of O-trialkylsilyl-N-alkyl-2-(1'-hydroxyprop-2'-enyl)imidazoles with aldehydes and ketones gives products of α- and γ-attack.Greater steric hindrance in the anion (triisopropyl vs t-butyldimethylsilyl) and in the aldehyde or ketone favours the γ-products.Sequential desilylation, N-methylation and treatment with base resulted in cleavage of these products to γ-lactones.The method was applied to the synthesis of (+/-)-cavernosine.