114049-50-2

Upstream product

• 152899-67-7 2-[(E)-1-(tert-Butyl-dimethyl-silanyloxy)-propenylsulfanyl]-pyridine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 146347-93-5 (E)-CH₃CHC(OSi(CH₃)2C(CH₃)3)SC₅H₄N 
• 79-03-8 propionyl chloride 
• 201809-42-9 2-((Z)-1-Triethylsilanyloxy-propenylsulfanyl)-pyridine 
• 101972-51-4 syn-3-cyclohexyl-3-hydroxy-2-methylpropanoic acid 
• 1250351-20-2 3-cyclohexyl-3-hydroxy-2-methylpropanoic acid 

Relevant academic research and scientific papers

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

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

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 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.

Dyotropic Rearrangement of Cycloalkyl β-Lactones. Formation of Spiro vs Fused Butyrolactones as a Function of Ring Size

Trans 3-substituted-4-cycloalkyl β-lactones 4 and 8 have been prepared via the condensation of appropriately substituted acetic acid dianions 1 with cyclohexane- or cyclopentanecarboxaldehyde to afford the corresponding diastereomerically pure β-hydroxy a

A NEW SYNTHESIS OF SUBSTITUTED SPIRO BUTYROLACTONES VIA DYOTROPIC REARRANGEMENT

Spiro butyrolactones bearing various α-substituents have been synthesized in three steps from acetic acid derivatives; the sequence employs a dyotropic rearrangement as its pivotal step.