Category: esters-buliding-blocks

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides was written by Liu, Bing;van Mechelen, Jeanine;van den Berg, Richard J. B. H. N.;van den Nieuwendijk, Adrianus M. C. H.;Aerts, Johannes M. F. G.;van der Marel, Gijsbert A.;Codee, Jeroen D. C.;Overkleeft, Herman S.. And the article was included in European Journal of Organic Chemistry in 2019.Synthetic Route of C16H22O11 This article mentions the following:

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bio-organic chem. and medicinal chem., yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation-reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on com. disaccharides, as shown in four examples, as well as on disaccharides that are not com. available and are synthesized for this purpose, as shown by a fifth example. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Synthetic Route of C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Synthetic Route of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Evaluation of stereochemically dense morpholine-based scaffolds as proline surrogates in β-turn peptides was written by Sladojevich, Filippo;Guarna, Antonio;Trabocchi, Andrea. And the article was included in Organic & Biomolecular Chemistry in 2010.Product Details of 133467-01-3 This article mentions the following:

Four peptides differing for the structure of the new morpholine-based heterocyclic compound acting as a turn inducer were synthesized in solution phase, and the conformational preferences were assessed by means of NMR anal. All spectroscopic data revealed an adaptive behavior of the turn peptides in generating turn conformations stabilized by intramol. hydrogen-bonds, despite the conformational changes of the turn inducer. Thus, this study suggests the possibility of functionalizing morpholine-containing β-turn peptides with no significant loss of the secondary framework. The 3,4-dihydro-2H-[1,4]oxazine-containing peptide showed a more compact structure stabilized by an addnl. γ-turn-forming hydrogen-bond experienced by the Gly amide proton. In the experiment, the researchers used many compounds, for example, Boc-D-Leu-OMe (cas: 133467-01-3Product Details of 133467-01-3).

Boc-D-Leu-OMe (cas: 133467-01-3) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Product Details of 133467-01-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

[Bis(2-methoxyethyl)amino]sulfur trifluoride, the Deoxo-Fluor reagent: application toward one-flask transformations of carboxylic acids to amides was written by White, Jonathan M.;Tunoori, Ashok Rao;Turunen, Brandon J.;Georg, Gunda I.. And the article was included in Journal of Organic Chemistry in 2004.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate This article mentions the following:

The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. The utility of this reagent was explored for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Combined bioderivatization and engineering approach to improve the efficiency of geraniol production was written by Wang, Xun;Xiao, Longjie;Zhang, Xinyi;Zhang, Jia;Zhang, Yu;Wang, Fei;Li, Xun. And the article was included in Green Chemistry in 2022.Recommanded Product: (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate This article mentions the following:

Constructing microbial factories offers a sustainable strategy for terpenoid synthesis; however, the accumulation of terpenoid products is often toxic to cells and hampers production yields. Here, we developed a bioderivatization strategy that successfully alleviates the toxicity of the end-product and maximizes the biochem. production of geraniol in Escherichia coli. We observed that the conversion of geraniol to less toxic geranyl acetate, which is an esterified derivative of geraniol, had a significant pos. effect on productivity. Subsequently, the high concentration and purity of geraniol was recovered by the combined hydrolysis of geranyl acetate and solid phase adsorption. These findings demonstrate that a combination of bioderivatization and engineering approaches for the biosynthesis of a relatively toxic chem. (geraniol) can mitigate cytotoxicity while further promoting production efficiency. Finally, the maximal titer of these engineering strategies accumulated 13.19 g L^-1 of geraniol by fed-batch fermentation in a 10-L fermentor. This study highlights the ability of this system to address the challenges associated with toxic geraniol accumulation. More broadly, the developed approach could also be considered for metabolic engineering of other similar chems. In the experiment, the researchers used many compounds, for example, (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3Recommanded Product: (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate).

(E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Recommanded Product: (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Barbituric acids. I. Synthesis of methylenebis(5-alkyl-barbituric acids) was written by Levina, R. Ya.;Godovikov, N. N.. And the article was included in Zhurnal Obshchei Khimii in 1954.Product Details of 10203-58-4 This article mentions the following:

CH₂(CO₂Et)₂ with paraform and 10% alc. KOH gave 60-70% CH₂[CH(CO₂Et)₂]₂ (I), b₅ 174-5°, n²⁰_D 1.4425, d₂₀ 1.119; mercuration with Hg(OAc)₂ gave the di-HgCl derivative, decompose 165-7° (from EtOH-Me₂CO). I (34 g.) added to 4.6 g. Na in 150 ml. dry EtOH, then RX added dropwise (the heating being interrupted for the addition), and the mixture heated until the basic reaction had nearly disappeared gave by the usual treatment the following (EtO₂C)₂CRCH₂CR'(CO₂Et)₂, (R, R’, % yield, b.p./mm., and n²⁰_D shown): Me, Me, 30.8, 190-1°/10, 1.4470; H, Me, 11.5, 78-9°/10, 1.4132; H, Et, 30.5, 74-5°/3, 1.4152; Et, Et, -, – (m. 62-3°), -; H, Pr, 32.3, 114-16°/3, 1.4198; Pr, Pr, 40, 206-8°/11 (m. 41-2°), -; Bu, Bu, 37.4, 198-9°/5, 1.4522; H, Bu, 30, 124-8°/18, 1.4226; H, PhCH₂, not isolated; PhCH₂,PhCH₂, 17, 240-5°/4 (m. 44°), -. The reactions yielded minor amounts of the polymers of I, m. 156° [cf. Bottomley and Perkin, J. Chem. Soc. 77, 306(1900)]. Alkylation attempts with iso-PrX, iso-BuX, iso-AmX (where X is halide), and cyclohexyl chloride, failed; only the corresponding RCH(CO₂Et)₂, polymer of I, and unreacted starting material were isolated. The reaction of the dialkylated esters with urea in the presence of EtONa yielded the following, 5,5′-methylenebis(5,1-alkylbarbituric acids) (alkyl group shown): H, 45%, decompose 300°; Me, 44.8%, m. 252-3°; Et, 61.7%, decompose 364-5°; Pr, 56.2%, decompose 358-9°; Bu, 25.4%, m. 235-8°; PhCH₂, 15.3%, m. 210-11°. The ring closures were run 18 hrs. at 120°. In the experiment, the researchers used many compounds, for example, Diethyl isobutylmalonate (cas: 10203-58-4Product Details of 10203-58-4).

Diethyl isobutylmalonate (cas: 10203-58-4) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Product Details of 10203-58-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Metabolomics and flavoromics analysis of chemical constituent changes during roasting of germinated Sacha inchi (Plukenetia volubilis L.) was written by Keawkim, Kannika;Na Jom, Kriskamol. And the article was included in Food Chemistry: X in 2022.Formula: C6H10O2 This article mentions the following:

This study examined the changes in metabolites together with the flavor profiles of germinated Sacha inchi seeds during roasting by using gas chromatog. The results indicated that roasting partially increased the browning index, amino acid levels, total phenolic content, and antioxidant capacity, but slightly decreased the levels of reducing sugars. Oxidized and rancid compounds were significantly decreased at a 180 °C roasting temperature Pyrazine, furan, and pyrrole were Maillard reaction products that were increased at 180 °C of roasting. Roasting at 145 °C for 45 min after germination for 4 days was determined to be the optimal conditions for roasting germinated Sacha inchi seeds, which reduced the off-flavor and burned taste. The roasted germinated Sacha inchi seed contains higher amino acids than raw seed, which could be used as an alternative source for food products and supplements. In addition, the roasted germinated seeds at 4 days were recommended for food applications. In the experiment, the researchers used many compounds, for example, 5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7Formula: C6H10O2).

5-Ethyldihydrofuran-2(3H)-one (cas: 695-06-7) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Formula: C6H10O2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Axially chiral amino acid scaffolds as efficient fluorescent discriminators of methanol-ethanol was written by Bag, Subhendu Sekhar;Jana, Subhashis. And the article was included in New Journal of Chemistry in 2017.Recommanded Product: tert-Butyl (3-ethynylphenyl)carbamate This article mentions the following:

The authors report a unique fluorescence sensor based on an axially chiral unnatural triazolyl aromatic amino acid scaffold (^ArTAA) for discrimination of methanol from ethanol via a switch on fluorescence response. All three sensors, the simple scaffold (^ArTAA), and the mono- (PyAm-^ArTAA) and bis-pyrenyl- (Py₂Am-^ArTAA) amides, show similar sensitivity and detection limit ranging from 0.5-2.1 volume/volume% of ethanol. The solid films of these sensors also are effective in sensing ethanol vapor via generation of a distinct and enhanced fluorescence signal. All the authors’ exptl. results suggest the role of axial chirality of the hairpin-shaped scaffold in differential solvation guided H-bonding interaction and discriminating between ethanol and methanol with a switch-on fluorescence response. In the experiment, the researchers used many compounds, for example, tert-Butyl (3-ethynylphenyl)carbamate (cas: 185619-66-3Recommanded Product: tert-Butyl (3-ethynylphenyl)carbamate).

tert-Butyl (3-ethynylphenyl)carbamate (cas: 185619-66-3) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Recommanded Product: tert-Butyl (3-ethynylphenyl)carbamate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A One-Pot Copper(II)-Catalyzed Tandem Synthesis of 2-Substituted Pyrrolo[1,2-b]pyridazin-4(1H)-ones was written by Tan, Cun;Xiang, Haoyue;He, Qian;Yang, Chunhao. And the article was included in European Journal of Organic Chemistry in 2015.Recommanded Product: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate This article mentions the following:

A one-pot copper(II)-catalyzed tandem synthesis of 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones, e.g., I, II, and III, from N-aminopyrroles was developed. This tandem reaction involves a Conrad-Limpach-type reaction, including the thermal condensation of N-aminopyrroles with the carbonyl group of β-oxo esters, followed by the cyclization of Schiff base intermediates. Compared to the traditional Conrad-Limpach quinoline synthesis, the authors applied the successful application of copper(II) as a catalyst in this transformation to furnish 2-substituted pyrrolo[1,2-b]pyridazin-4(1H)-ones for the first time. Most of the substrates bearing electron-donating (EDG) and electron-withdrawing (EWG) groups worked well with this procedure. The corresponding products could be converted directly into diverse pyrrolo[1,2-b]pyridazines for drug discovery and materials science. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Recommanded Product: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate).

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Recommanded Product: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis of 3-C-Branched Kdo Analogues via Sonogashira Coupling of 3-Iodo Kdo Glycal with Terminal Alkynes was written by Fan, Wenjing;Chen, Yan;Lou, Qixin;Zhuang, Liqin;Yang, You. And the article was included in Journal of Organic Chemistry in 2018.COA of Formula: C10H14O4 This article mentions the following:

A highly efficient approach for the synthesis of 3-C-branched mono- and di-3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) enyne analogs is developed for the first time based on Sonogashira coupling of terminal alkynes with 3-iodo Kdo glycal obtained by the NIS/TMSOTf-promoted one-step reaction from peracetylated Kdo Et ester. Further transformation of 3-C-branched mono- and di-Kdo enyne analogs by asym. hydrogenation and saponification provided 2-deoxy-β-carboxyl Kdo analogs in a stereocontrolled mode. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9COA of Formula: C10H14O4).

Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.COA of Formula: C10H14O4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Cycloisomerization/Oxidation of Electron-Deficient Dienynes was written by Kramer, Nicholas J.;Hoang, Tung T.;Dudley, Gregory B.. And the article was included in Organic Letters in 2017.Electric Literature of C10H14O4 This article mentions the following:

A rhodium-catalyzed cycloisomerization and oxidation of tethered dienynes for the synthesis of indans, e.g. I, is described. An auxiliary fragmentation/olefination method (also described herein) provides novel access to tethered alkyne-dienoate substrates. The reported method circumvents current limitations in and expands the scope of inverse-demand Diels-Alder-type cycloadditions Traditional discovery substrates involving malonate-, ether- and sulfonamide-based tethers are problematic in the current methodol., underscoring the unique virtue of neopentylene-tethered substrates for reaction discovery. In the experiment, the researchers used many compounds, for example, Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9Electric Literature of C10H14O4).

Diethyl 2-(prop-2-yn-1-yl)malonate (cas: 17920-23-9) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Electric Literature of C10H14O4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics