183245-66-1

Upstream product

• 21080-41-1 β-hydroxy-benzenepentanoic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 156662-12-3 2-[1-(tert-Butyl-dimethyl-silanyloxy)-vinylsulfanyl]-pyridine 
• 19060-98-1 Triethylsilanyl-ethenone 
• 42414-77-7 (dimethylphenylsilyl)ketene 
• 506-96-7 Acetyl bromide 
• 75-36-5 acetyl chloride 
• 100-39-0 benzyl bromide 
• 53376-62-8 ethyl 3-hydroxy-5-phenylpentanoate 
• 4071-85-6 trimetylsilylketene 
• 199989-15-6 2-(1-triethylsilanyloxy-vinylsulfanyl)-pyridine 

Downstream Products

• 218782-74-2 (+/-)-1-(O-benzyl)-4-((2-phenyl)ethyl)-2-azetidinone 
• 147526-02-1 (+/-)-4-(2-phenylethyl)-2-azetidinone 
• 261159-45-9 (R)-4-(2-phenylethyl)oxetane-2-one 
• 214853-90-4 (S)-4-(2-phenylethyl)oxetane-2-one 

Relevant academic research and scientific papers

The mechanism of caseinolytic protease (ClpP) inhibition

Catch me if you can: The ClpP protease mediates protein homeostasis and can be efficiently inhibited by β-lactones. A combination of molecular docking, mutagenesis, activity-based protein profiling, and kinetics studies now reveals the mechanism of ClpP inhibition. A hydrophobic pocket next to the active site allows binding of long aliphatic and aromatic residues. The preferred stereoisomer binds into the oxyanion hole. Copyright

MNBA-mediated β-lactone formation: Mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin

Various β-lactones were prepared from β-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

Catalyzed acyl halide-aldehyde cyclocondensations. New insights into the design of catalytic cross aldol reactions

Substoichiometric quantities (2.5-20 mol%) of Al(SbF6)3 catalyze the di(isopropyl)ethylamine-mediated cyclocondensation of various acyl halides and enolizable aldehydes to afford β-lactones in good yields (58-93%). These reactions ar

A stereocomplementary approach to β-lactones: Highly diastereoselective synthesis of cis-β-lactones, a β-chloro acid, and a tetrahydrofuran

(matrix presented) In the course of mechanistic studies of the ZnCl2-mediated tandem Mukaiyama aldol-lactonization reaction of aldehydes and thiopyridyl ketene acetals, a stereocomplementary reaction employing SnCl4 was discovered. T

Process for producing a β-lactone derivative

The present invention provides a process for producing a β-lactone derivative by reacting an aldehyde represented by formula (1): wherein R represents a C1-C15 alkyl group which may be substituted by an aryl group, a C2-C15 alkenyl group, a 5-7-membered a

Synthesis and inhibitory action on HMG-CoA synthase of racemic and optically active oxetan-2-ones (β-Lactones)

A homologous series of both C3-unsubstituted and C3-methyl substituted oxetan-2-ones (β-lactones) was investigated as potential inhibitors of yeast 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) synthase. Several reported methods for racemic β-lactone synthesis were studied for preparation of the target series. In addition, a novel aluminum-based Lewis acid obtained by combination of Et2AlCl with (1R,2R)-2-[(diphenyl)hydroxymethyl] cyclohexan-1-ol was studied for the asymmetric [2+2] cycloaddition of aldehydes and trimethylsilylketene. This Lewis acid exhibited good reactivity but variable enantioselectivity (22-85% ee). In in vitro assays using both native and recombinant HMG-CoA synthase from Saccharomyces cerevisiae, oxetan-2-ones mono-substituted at C4 with linear alkyl chains gave IC50s that decreased monotonically with chain length up to 10 carbons and then rose rapidly for longer chains. The trans isomers of 3-methyl-4-alkyl-oxetan-2-ones showed a similar trend but had 1.3- to 5.6-fold lower IC50s. The results imply a substantial hydrophobic pocket in this enzyme that interacts with both C-3 and C-4 substituents of oxetan-2-one inhibitors. Copyright (C) 1998 Elsevier Science Ltd.

Studies of the asymmetric [2+2] cycloaddition of silylketenes and aldehydes employing Ti-TADDOL catalysts

Ti-TADDOL catalysts provide good reactivity and moderate enantioselectivity in the asymmetric [2+2] cycloaddition of silyl ketenes and aldehydes. The effects of potential bidentate chelation of benzyloxy substituted aldehydes and of the steric size of the ketene silyl group were studied.

Studies of the tandem mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-Panclicin D

A concise and highly diastereoselective route to β-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (-) - Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving group of the ketene acetal.