105643-82-1Relevant academic research and scientific papers
Selective synthesis of α,α-dideuterio alcohols by the reduction of carboxylic acids using Smi2 and D2O as deuterium source under set conditions
Szostak, Michal,Spain, Malcolm,Procter, David J.
, p. 5052 - 5055 (2014)
The first general method for the chemoselective synthesis of α,α-dideuterio alcohols directly from feedstock carboxylic acids under single electron transfer conditions using SmI2 is reported. This reaction proceeds after the activation of Sm(II
Synthetic method of alpha-monodeuterated alcohol compound and deuterated drug
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Paragraph 0037; 0041-0044, (2021/06/12)
The invention provides an alpha-monodeuterated alcohol compound and a reduction deuteration method of an aldehyde ketone compound for preparing the alpha-monodeuterated alcohol compound. The aldoketone compound shown in a general formula (1) reacts with a divalent lanthanide transition metal compound and a deuterium donor reagent in an organic solvent I to generate the alpha-monodeuterated alcohol compound shown in a general formula (2). The invention establishes a reduction deuteration method of an aldehyde ketone compound based on a single electron transfer reduction deuteration reaction, and the method is used for preparing the alpha-monodeuterated alcohol compound shown in a general formula (2) as well as deuterated derivatives of aldehyde ketone drugs, hormones and natural products of the alpha-deuterated alcohol compounds. The method has the advantages of high product deuteration rate, good regioselectivity, good chemical selectivity, low reagent price, simple operation, mild conditions and wide substrate application range. Compared with an existing H/D exchange method, the deuterium donor reagent is small in dosage, the cost can be remarkably reduced, and the utilization rate of deuterium atoms is increased.
Synthesis of α-Deuterioalcohols by Single-Electron Umpolung Reductive Deuteration of Carbonyls Using D 2O as Deuterium Source
Li, Hengzhao,Hou, Yuxia,Lai, Zemin,Ning, Lei,Li, Ailing,Li, Yixuan,An, Jie
supporting information, p. 1241 - 1245 (2021/07/02)
Deuterium incorporation can effectively stabilize the chiral centers of drug and agrochemical candidates that hampered by rapid in vivo racemization. In this work, the synthetically challenging chiral-center deuteration of alcohols has been achieved via a single-electron umpolung reductive-deuteration protocol using benign D 2O as deuterium source and mild SmI 2as electron donor. The broad scope and excellent functional group tolerance of this method has been showcased by the synthesis of 43 respective α-deuterioalcohols in high yields and ≥98% deuterium incorporations. The potential application of this versatile method has been exemplified in the synthesis of 6 deuterated drug derivatives, 1 deuterated human hormone, and 3 deuterated natural products. This method using D 2O is greener and more efficient compared to traditional pyrophoric-metal-deuteride-mediated reductive deuterations.
