2020
DOI: 10.1016/j.tetlet.2020.152642
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Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays

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Cited by 5 publications
(4 citation statements)
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“…For example, deuterated acetone, in addition to being an NMR solvent, is an attractive building block for the introduction of a gem-ditrideuteromethyl fragment. This moiety is recovered in the labeled aroma fragment β-ionone 380 as well as in a leukotriene C4 synthase inhibitor. 381 MK 3814 was investigated as a potential treatment for Parkinson's disease.…”
Section: Multistep Syntheses With Deuterium Incorporationmentioning
confidence: 99%
“…For example, deuterated acetone, in addition to being an NMR solvent, is an attractive building block for the introduction of a gem-ditrideuteromethyl fragment. This moiety is recovered in the labeled aroma fragment β-ionone 380 as well as in a leukotriene C4 synthase inhibitor. 381 MK 3814 was investigated as a potential treatment for Parkinson's disease.…”
Section: Multistep Syntheses With Deuterium Incorporationmentioning
confidence: 99%
“…This purification process resulted in the isolation of a molecule, I-4 (2.8 mg, t R = 40 min). This molecule, I-4 , was identified as β -cyclocitral by comparing the MS and 1 H NMR spectral data with the previous literature [ 30 , 31 ]. HR ESI-TOF-MS m/z [M+H] + 153.1217; 1 H NMR (500 MHz, Chloroform-d) Δ 10.13 (s, 1H), 2.19 (t, J = 6.3 Hz, 2H), 2.09 (s, 3H), 1.67–1.58 (m, 2H), 1.47–1.41 (m, 2H), 1.20 (s, 6H).…”
Section: Methodsmentioning
confidence: 87%
“…6b). Additionally, we utilized the developed method to access deuterated Bezafibrate (19) 57 , a medication used to regulate lipid levels in the blood. Treatment of d2-TT salt 2f with aryl bromide 4b resulted in the efficient formation of the 5fb product.…”
Section: Synthetic Applicationsmentioning
confidence: 99%
“…This technique enables the introduction of both deuterium atoms and functional groups in a single step, resulting in the construction of a target molecule with easily controllable deuterated sites and a high level of deuterium incorporation. Although this method has been utilized in the synthesis of deuterium-containing drugs [16][17][18][19][20] , its progress has been hindered by the limited availability of readily accessible deuterated reagents. Alkyl halides (I, Br, and Cl) and pseudohalides (OTs, OTf) are widely applied and abundant electrophilic alkylation reagents within the realm of organic synthesis.…”
mentioning
confidence: 99%