5405-40-3

Usage

Uses

Used in Asymmetric Catalysis:
L-PANTOLACTONE is used as a reactant for the preparation of tunable ligands, specifically carbohydrate-derived diarylphosphinites. These ligands are crucial in asymmetric catalysis, a field that focuses on the selective synthesis of chiral molecules with a single enantiomer, which is essential in the pharmaceutical industry for the development of more effective and safer drugs.
Used in Hydrovinylation of Styrene Derivatives:
L-PANTOLACTONE is also utilized in the hydrovinylation of styrene derivatives, a chemical reaction that involves the addition of a hydrogen atom and an alkyl group to a vinyl compound. This process is significant in the synthesis of various industrial chemicals and materials, such as polymers and pharmaceutical intermediates.

InChI:InChI=1/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m1/s1

Upstream product

• 79-50-5 pantolactone 
• 13031-04-4 ketopantolactone 
• 28227-35-2 (RS)-2-acetoxy-3,3-dimethyl-γ-butyrolactone 
• 1902-01-8 DL-sodium pantoate 
• 123355-74-8 (R,R)-(-)-trans-2,3-bis(diphenylhydroxymethyl)-1,4-dioxaspiro<4.5>decane * (S)-(-)-pantolactone 
• 599-04-2 (R)-Pantolacton 
• 75-36-5 acetyl chloride 
• 259107-29-4 2S-3,3-dimethyl-2-hydroxy-4-methoxybutanoic acid N-methyl amide 
• 259107-28-3 2S,5S,6R-4,5-dimethyl-6-phenyl-2-(1,1-dimethyl-2-methoxy ethyl) morpholin-3-one 
• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 924-44-7 glyoxylic acid ethyl ester 
• 78-84-2 isobutyraldehyde 
• 895532-73-7 (S)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropan-1-ol 
• 1377411-53-4 (S)-3-(benzyloxy)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethylpropyl acetate 

Downstream Products

• 134734-33-1 O-(4-nitro-benzoyl)-L-pantolactone 
• 101776-81-2 N-phenethyl-L-pantamide 
• 20664-72-6 O-(toluene-4-sulfonyl)-L-pantolactone 
• 27979-04-0 (3aS)-1,3-dibenzyl-6c-((S)-4,4-dimethyl-2-oxo-(3ar,6ac)-tetrahydro-furan-3-yloxy)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 27979-04-0 (3aR)-1,3-dibenzyl-6t-((S)-4,4-dimethyl-2-oxo-(3ar,6ac)-tetrahydro-furan-3-yloxy)-tetrahydro-furo[3,4-d]imidazole-2,4-dione 
• 74561-18-5 dexpanthenol 
• 20374-33-8 (S)-3-(benzyloxy)-4,4-dimethyldihydrofuran-2(3H)-one 
• 86809-23-6 l-1-Phenoxy-2-hydroxy-3-ammoniumpropane-L-pantoate 
• 300578-08-9 (R)-4,4-Dimethyl-3-((2S,3R)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 
• 300578-06-7 (R)-4,4-Dimethyl-3-((2R,3S)-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-dihydro-furan-2-one 
• 1112-32-9 L-pantoic acid 
• 924961-36-4 (2S)-2-tert-butyldiphenylsiloxy-3,3-dimethyl-4-butanolide 
• 128271-03-4 (S)-4-((2R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-3,3-dimethyl-tetrahydro-pyran-2-ylmethyl)-[1,3]dioxolan-2-one 
• 111080-21-8 (S)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-oxirane 

Relevant academic research and scientific papers

Industrial kinetic resolution ofd,l-pantolactone by an immobilized whole-cell biocatalyst

Immobilized whole-cells ofPichia pastorisharboring recombinantd-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution ofd,l-pantolactone. The immobilized whole-cell biocatalyst exhibited good catalytic stability, which was applied for stereospecific hydrolysis ofd-pantolactone for up to 56 repeated batch reactions without obvious loss in the catalytic activity and enantioselectivity.

Preparation method of hydroxyaldehyde and method for resolving optical isomer by using electrodialysis technology

The present invention provides a process for preparing hydroxyaldehydes using an immobilized catalyst, wherein the immobilized catalyst comprises a solid support and a tertiary amine-based functionalgroup. The invention also provides a method for preparing a polyhydroxy alcohol compound and a polyhydroxy acid compound. The invention further provides a method for splitting the optical isomer fromthe raceme through electrodialysis.

Synthesis method of chiral 2-hydroxy-1, 4-dicarbonyl compound and pantoic acid lactone

The invention discloses a chiral 2-hydroxy-1, 4-dicarbonyl compound synthesized by catalyzing asymmetric Aldol reaction of fatty aldehyde and glyoxylate or fatty aldehyde and acylformaldehyde monohydrate by taking tetrapeptide TP or an enantiomer ent-TP thereof as a chiral catalyst, and application of a synthetic product. The method for synthesizing the chiral 2-hydroxy-1, 4-dicarbonyl compound through the asymmetric Aldol reaction is shown as a formula 1 and a formula 2. The asymmetric Aldol reaction of fatty aldehyde and glyoxylate or fatty aldehyde and acylformaldehyde monohydrate is catalyzed to synthesize the optically active 2-hydroxy-1, 4-dicarbonyl compound, then the optically active pantoic acid lactone can be further synthesized, and the method has advantages of mild reaction conditions, easy operation, low catalyst consumption, high yield and the like, and can synthesize the 2-hydroxy-1, 4-dicarbonyl compounds with two configurations by using tetrapeptide and the enantiomerthereof.

Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands

A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting materials. By capitalizing from the capacity of prolineamides to act as both an organocatalyst and a transfer hydrogenation ligand, catalyst repurposing allowed the development of an operationally simple, economic, and efficient sequential catalysis approach.

STEREOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY-ENRICHED PANTOLACTONE

The present invention relates stereoselective synthesis of enantiomerically enriched pantolactone.

Wittig Rearrangements of Boron-Based Oxazolidinone Enolates

[2,3]-Sigmatropic rearrangements (Wittig rearrangements) of α-alkoxy oxazolidinone enolates are described. Whereas alkali metal enolates fail, owing to facile deacylation, boron enolates generated from di-n-butylboron triflate and triethylamine rearranged in good yields and high selectivities with exceptions noted. IR and NMR spectroscopies show the boron is chelated by the α-alkoxy group rather than the more distal oxazolidinone carbonyl in the complex and enolate. The rearrangement product contains a boron alkoxide that remains unchelated by either carbonyl. Optimization was guided by density functional theory computations, suggesting that valine-derived oxazolidinones would be superior to the phenylalanine-derived analogues.

A thermoregulated phase-separable chiral Pt nanocatalyst for recyclable asymmetric hydrogenation of α-ketoesters

The design and preparation of a chiral Pt nanocatalyst system possessing thermoregulated phase-separation property and its application in recyclable asymmetric hydrogenation of α-ketoesters are presented.

Porous Aerogels from Shape-Controlled Metal Nanoparticles Directly from Nonpolar Colloidal Solution

Porous architectures of noble metal nanocrystals are promising for many catalytic as well as for fuel cell applications. Here we present the synthesis of porous, extremely lightweight aerogels of self-supported Pt nanocubes and nanospheres by direct destabilization from nonpolar colloidal solution using hydrazine monohydrate (N2H4·H2O) as gelation reagent. The template-free voluminous lyogels of the Pt nanocrystals are converted to macroscopic solid aerogel monoliths by supercritical drying. The aerogels from Pt nanocubes mostly exhibit (100) as the exposed crystal facets throughout the entire monolithic surface, while the aerogels from quasi-spherical Pt nanocrystals exhibit many crystal facets such as (111) and (100). Furthermore, the aerogels exhibit remarkably low densities of ～0.19 g cm-3 ± 0.038 g cm-3 (～0.9% of bulk Pt) and a specific surface area in the range of ～6400-7000 m2 mol-1. The nanocube gels show better catalytic performance than the nanosphere gels when employed for asymmetric hydrogenation reaction, which is exemplarily shown for 4,4-dimethyldihydrofuran-2,3-dione to d-/l-pantolactone conversion with an excess of 9% for the d-enantiomer. Owing to their high specific surface area and certain type of exposed crystal facets, Pt aerogels developed here are highly promising for possible future applications in facet selective catalytic reactions.

A ionic liquid under the conditions of the asymmetric hydrogenation process of synthesizing method of D - pantolactone

The invention relates to a method for synthesizing D-pantolactone through asymmetric hydrogenation under an ionic liquid condition. The method adopts a homogeneous-phase asymmetric hydrogenation system which is composed of a chiral catalyst formed by chiral diphosphine ligand and a rhodium catalyst, a polyether alkyl guanidine salt ionic liquid, ketopantolactone and benzene or toluene; and asymmetric hydrogenation is carried out a certain reaction temperature and hydrogen pressure. According to the method provided by the invention, the immobilization effect of the ionic liquid on the chiral catalyst is utilized, separation and circulation of the chiral catalyst are realized through simple liquid-liquid separation, and the chiral catalyst can be cyclically used for a plurality of times; and the conversion rate of pantolactone or stereoselectivity of D-pantolactone is not obviously decreased.

Missing Linker Defects in a Homochiral Metal-Organic Framework: Tuning the Chiral Separation Capacity

Efficient chiral separation remains a very challenging task due to the identical physical and chemical properties of the enantiomers of a molecule. Enantiomers only behave differently from each other in the presence of other chiral species. Homochiral metal-organic frameworks (MOFs) have received much attention for their promising enantioseparation properties. However, there are still challenges to overcome in this field such as high enantiomeric separation. Structural defects play an important role in the properties of MOFs and can significantly change the pore architecture. In this work, we introduced missing linker defects into a homochiral metal-organic framework [Zn2(bdc)(l-lac)(dmf)] (ZnBLD; bdc = 1,4-benzenedicarboxylic acid, l-lac = l-lactic acid, dmf = N,N′-dimethylformamide) and observed an increase in enantiomeric excess for 1-phenylethanol of 35% with the defective frameworks. We adjusted the concentration of monocarboxylic acid ligand l-lactic acid by varying the ratio of Zn2+ to ligand from 0.5 to 0.85 mmol. Additionally, a defective framework was synthesized with propanoic acid as modulator. In order to elucidate the correlation between defects and enantiomeric excess, five characterization techniques (FTIR, TGA, 1H NMR, ICP, and PXRD) were employed. Full width at half-maximum analysis (fwhm) was performed on the powder X-ray diffraction traces and showed that the higher concentration of monocarboxylic acid MOFs were isostructural but suffered from increased fwhm values.