A Lewis acid-promoted Pinner reaction

Pfaff, Dominik; Nemecek, Gregor; Podlech, Joachim

doi:10.3762/bjoc.9.179

Cited by 21 publications

(14 citation statements)

References 20 publications

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“…The synthesis of the imidate derivative was carried out using a base in order to promote the formation of an alkoxide and the addition of the formed anion to an electron‐poor nitrile, also known as Pinner reaction . Due to the choice of the base (sodium hydride) and prolonged reaction times (4 h), the formation of the α‐anomer of the resulting protected glucopyranosyl trichloroacetimidate was favoured .…”

Section: Resultsmentioning

confidence: 99%

“…[35] Due to the choice of the base (sodium hydride) and prolonged reaction times (4 h), the formation of the α-anomer of the resulting protected glucopyranosyl trichloroacetimidate was favoured. [35] Due to the choice of the base (sodium hydride) and prolonged reaction times (4 h), the formation of the α-anomer of the resulting protected glucopyranosyl trichloroacetimidate was favoured.…”

Section: Coupling Of Protected Glucose With Cholesterolmentioning

confidence: 99%

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Novel Method for the Synthesis of Cholesteryl Glucosides starting from Disaccharides

Weiss

Neu

Ludwig

et al. 2018

Euro J Lipid Sci & Tech

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Steryl glucosides (SG) and acylated steryl glucosides (ASG) are natural components of plant cell membranes and present in different concentrations in various plant foods. Currently, their positive effects on human health are under investigation. The present work presents a new and efficient synthesis method for cholesteryl glucosides starting from disaccharides. A five‐step synthesis protocol is done to obtain the desired product in 35% overall yield. In the first step, the hydroxy groups of the starting material sucrose are protected using benzyl ethers. After the subsequent acidic hydrolysis the obtained pyranosyl moiety of the disaccharide is transformed to its trichloroacetimidate derivative. Next, the formation of the glycosidic bond to cholesterol is performed and catalytic transfer hydrogenation in order to remove the protecting groups leads to the desired product. In this context, APCI‐MS‐TOF has turned out to be an excellent analytical tool for the high sensitive analysis of SG as well as intermediates. Practical Applications: Due to the comparatively high amounts of SG and ASG in seeds and oils, not only the food industry but also in biodiesel production, these natural compounds are of increasing interest. However, analysis of the compounds is difficult, commercially available pure standard materials are costly and their synthesis often requires time‐consuming work‐up procedures. The described preparation method allows the synthesis of cholesteryl glucosides which can be used as reference or standard material for the quantitative analysis of phytosteryl glucosides in plant derived samples. The general synthesis method could be also applied to other SG and ASG derivatives. Cholesteryl glucosides are synthesized using a new and efficient five‐step synthesis protocol starting from disaccharides. The preparation method provides products with good overall yield and high purity and, therefore, the synthesized glucosides can be used as reference or standard material for the quantitative analysis of phytosteryl glucosides in plant derived samples. APCI‐MS‐TOF is extensively used as analytical tool for the sensitive analysis of cholesteryl glucosides as well as intermediates.

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Section: Resultsmentioning

confidence: 99%

Section: Coupling Of Protected Glucose With Cholesterolmentioning

confidence: 99%

Novel Method for the Synthesis of Cholesteryl Glucosides starting from Disaccharides

Weiss

Neu

Ludwig

et al. 2018

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

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“…The Pinner reaction involves the reaction between an alcohol (either aliphatic or aromatic with no steric hindrance) and a nitrile (either aliphatic or aromatic). Carbonitriles in the presence of hydrochloric acid react with alcohols to give imidate hydrochlorides as reported by Pfaff et al [14] when they obtained good yields from reacting benzylic carbonitriles with primary alcohol. The reaction mechanism involves activation of nitrilium chloride from protonation of nitrile-nitrogen leading to the alcohol attacking the nitrile carbon [15].…”

Section: Introductionmentioning

confidence: 81%

Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate

Bamigboye

Abbo

Kwong

et al. 2021

Zeitschrift Für Kristallographie - Crystalline Materials

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X-ray crystallography on [EtOC(=O)N(H)C(=N+H2)NH2]Cl·½H2O (1) shows the asymmetric unit to comprise two independent cations, two chloride anions and crystal water. The main conformational difference between the cations is seen in the relative orientation of the ethyl groups; geometry-optimisation confirms the all-trans conformation is the most stable. The remaining parts of the cations are co-planar and feature intramolecular N–H···O(carbonyl) hydrogen bonds. An analysis of the C–N bonds suggests substantial delocalisation of the positive charge over the CN3 atoms. In the crystal, columns comprising the first independent cation are surrounded by four columns of the second cation within a network of water-O–H···Cl, N–H···Cl and N–H···O(water, carbonyl) hydrogen bonds, many of which are charge-assisted. The packing has been further investigated by Hirshfeld surface analysis, molecular electrostatic potential and interaction energy calculations. The charge-assisted N–H···Cl hydrogen bonds are significantly stronger than the water-O–H···Cl interactions consistent the distribution of the positive charge over the CN3 atoms.

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“…In the case of PF-00835231, the Cysteine thiol group forms a covalent bond with the ketone group of the terminal α-hydroxyketone moiety to give a hydrogen bond-stabilized hemithioacetal, together with additional hydrogen bonds with a number of other key residues. Nirmatrelvir occupies the active site in a similar way, with Cys-145 binding covalently to its nitrile group via a Pinner-like reaction and several hydrogen bonds [ 102 , 161 ]. ( Fig.…”

Section: Discussionmentioning

confidence: 99%

The effect of various compounds on the COVID mechanisms, from chemical to molecular aspects

Mahmoudi

Dehkordi

Asgarshamsi

2022

Biophysical Chemistry

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A Lewis acid-promoted Pinner reaction

Cited by 21 publications

References 20 publications

Novel Method for the Synthesis of Cholesteryl Glucosides starting from Disaccharides

Novel Method for the Synthesis of Cholesteryl Glucosides starting from Disaccharides

Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate

The effect of various compounds on the COVID mechanisms, from chemical to molecular aspects

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