Synthesis technology for preparing deuterated aldehyde compound

Abstract

The invention relates to a synthetic method for preparing a deuterated aldehyde compound in the technical field of medicines, and belongs to the technical field of chemical pharmacy. Specifically, the invention relates to a synthetic method of deuterated aldehyde as shown in formula I. The general formula of the deuterated aldehyde compound is as shown in formula I in the specification. The deuterated aldehyde compound is generated by taking corresponding aldehyde as a substrate, thiol as a catalyst, heavy water as a deuterium source and esters as a reaction solvent under light irradiation. The deuterated aldehyde can be used for synthesizing other types of deuterated compounds. # imgabs0 #

Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis, and in particular to a method for preparing deuterated aldehyde by H / D exchange. Technical Background

[0002] Deuterium is an isotope of hydrogen. Deuterated compounds have important and wide applications in many fields. Deuterated compounds can effectively reduce the interference of hydrogen in NMR experiments, thereby improving the clarity and resolution of the spectrum. This allows researchers to analyze the structure and dynamic processes of molecules more accurately. Deuterated compounds may behave differently from their hydrogen counterparts in chemical reactions. By using deuterated compounds, researchers can track the transfer and participation of hydrogen atoms in the reaction process, thereby gaining a deeper understanding of the reaction mechanism. In the drug development process, deuterated compounds can be used to study the metabolic pathways and bioavailability of drugs. The introduction of deuterium may change the metabolic rate of drugs, thereby providing important information about drug stability and efficacy. Deuterated compounds are often used as biomarkers to help scientists track the distribution and metabolism of molecules in organisms, especially in biochemistry and molecular biology research. The introduction of deuterated compounds can affect the physicochemical properties of molecules, such as melting point, boiling point and solubility, which provides a new perspective for studying the interactions and behaviors of molecules. Therefore, the efficient preparation of deuterated compounds is of great significance.

[0003] At present, the methods for drug deuteration can be roughly divided into three categories: hydrogen-deuterium exchange (HDE), dehalogenation and reductive deuteration. Among them, HDE has the highest efficiency because it does not require the introduction and conversion of functional groups. With the rapid development of photochemistry in recent years, free radical-mediated HDE has gained widespread attention. The key steps usually include the generation of carbon radicals and the deuteration of carbon radicals. Carbon radicals can be generated by proton-coupled electron transfer (PCET) or photocatalyst-catalyzed hydrogen atom transfer (HAT). The thiol-d1 generated in situ by the reaction of HDE with heavy water usually serves as a deuterium atom donor to complete the deuteration step.

[0004] Aldehydes are not only widely present in natural products, but also play a vital role in chemical and drug synthesis. Deuterated aldehydes can be used to prepare various types of deuterated compounds. Among various methods, photocatalytic hydrogen-deuterium exchange (HDE) of aldehydes has become an ideal method due to its high synthesis efficiency. However, the current photocatalytic HDE method requires the use of a photocatalyst. The use of photocatalysts will bring about the cost of catalyst synthesis and the cost of removal during the purification process, which is not conducive to industrial promotion. Summary of the invention

[0005] The object of the present invention is to provide a method for preparing deuterated aldehydes. Deuterated aldehydes are prepared by HDE under 380nm light with aldehydes as substrates, heavy water as deuterium source, thiols as additives, and esters as solvents. The method has the advantages of high operability, good deuteration effect, and no catalyst.

[0006] The technical solution adopted by the present invention to solve its technical problem is:

[0007] A method for preparing a deuterated aldehyde by HDE, wherein the aldehyde is used as a substrate, and a reaction is carried out under light irradiation in a reaction system consisting of a thiol, a deuterium source reagent, and a solvent; after the reaction is completed, the product is separated and purified to obtain a compound shown in formula I.

[0008]

[0009] Where R 1 is aryl, substituted aryl, polycyclic aryl, heterocyclic aryl, substituted heterocyclic aryl, polycyclic aryl, C 1-18 Alkyl, C 1-10 Cycloalkyl. Including but not limited to the following compounds:

[0010]

[0011] The preferred molar ratio of substrate, thiol and heavy water is 1:0.05-0.3:40-100.

[0012] Preferably, the thiol is selected from one or two of triisopropylsilylmercaptan, triphenylsilylmercaptan and phenylethylmercaptan.

[0013] Preferably, the deuterium source reagent is selected from heavy water.

[0014] The anhydrous solvent is selected from anhydrous acetonitrile, anhydrous acetone, anhydrous 1,2-dichloroethane, anhydrous dichloromethane, anhydrous chloroform, anhydrous ethyl acetate, anhydrous methyl propionate, anhydrous ethyl propionate, anhydrous methyl formate, anhydrous ethyl formate or a mixed solvent of any two thereof. Preferably, esters are used as solvents.

[0015] The wavelength of the light used may be any wavelength or wavelength band between 365 nm and 450 nm, but is preferably any wavelength or wavelength band between 380 nm and 400 nm.

[0016] The reaction time is 6-48 hours.

[0017] The beneficial effects of the present invention are: 1) no additional photocatalyst is required in the photoreaction, and it can be effectively completed using a cheap deuterium source, the reaction is highly operable, and the deuteration effect is good; 2) the process method has good universality and can be used for the preparation of a variety of deuterated aldehyde products; it is safe, green, and cheap. DETAILED DESCRIPTION

[0018] The technical solution of the present invention is further described in detail below through specific embodiments.

[0019] In the present invention, unless otherwise specified, the raw materials and equipment used can be purchased from the market or are commonly used in the art. The methods in the following embodiments, unless otherwise specified, are all conventional methods in the art.

[0020] Example 1, Preparation of Compound 2a

[0021] At room temperature, under an argon atmosphere, p-tolualdehyde (48uL, 0.4mmol, 1.0 equivalent), triisopropylsilanethiol (4.4uL, 5mol%), heavy water (320uL, 40equiv) and 2.0mL of anhydrous ethyl acetate were added to the reaction tube. The solution was degassed by freeze-pump-thaw and then plugged with a rubber stopper. The reaction solution was stirred for 6 hours under a 380nm LED. After the reaction was completed, the reaction solution was concentrated. After the reaction was completed, the reaction solution was concentrated and the target compound 2a was separated by column chromatography as a yellow oil. (38mg, 79% yield, 94% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.97 (s, 0.05H), 7.78 (d, J = 7.6Hz, 2H), 7.34 (d, J = 7.7Hz, 2H), 2.44 (s, 3H). 13 C NMR (100MHz, CDCl3) δ191.99–191.41(m),145.56,134.16,129.85,129.72.

[0022] The preparation methods of the remaining compounds are the same as those of 2a. Various deuterated aldehyde compounds can be obtained after the above reaction conditions. The results are shown in Table 1:

[0023] Table 1

[0024]

[0025] Example 2, Preparation of Compound 2b

[0026] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a yellow oil 2b (32.00 mg, 66% yield, 92% D ratio by 1 1H NMR). 1H NMR (400MHz, CDCl3) δ9.99 (s, 0.07H), 7.69 (d, J = 8.5Hz, 2H), 7.47–7.40 (m, 2H), 2.44 (s, 3H). 13 C NMR (100MHz, CDCl3) δ138.94,135.31,130.03,128.89,127.24.

[0027] Example 3, Preparation of Compound 2c

[0028] The method was the same as in Example 1, except that 30 mol% of triisopropylsilanethiol was used and the reaction was continued for 24 hours to obtain yellow oil 2c (48.70 mg, 99% yield, 97% D ratio by 1 1H NMR). 1 H NMR (400MHz, CDCl3) δ9.88 (s, 0.03H), 7.84 (d, J = 8.8Hz, 2H), 7.00 (d, J = 8.8Hz, 2H), 3.89 (s, 3H). 13 C NMR (100MHz, CDCl3) δ190.82–190.20(m),164.62,131.98,129.94–129.79(m),114.32,55.59.

[0029] Example 4, Preparation of Compound 2d

[0030] The method is the same as that of Example 1, except that 30 mol% of triisopropylsilanethiol is used and the reaction is carried out for 48 hours to obtain a white solid 2d (20.3 mg, 51% yield, 83% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.88 (s, 0.15H), 7.84 (d, J = 8.7Hz, 2H), 7.45–7.34 (m, 5H), 7.11–7.05 (m, 2H), 5.15 (s, 2H). 13 CNMR(100MHz, CDCl3)δ190.84–190.27(m),163.77,135.96,132.03,128.76,128.36,127.51,115.17,77.25,70.29.

[0031] Example 5, Preparation of Compound 2e

[0032] The method is the same as Example 1, except that 30 mol% of triisopropylsilanethiol is used. The reaction is carried out for 48 hours to obtain a yellow oil 2e (20.3 mg, 51% yield, 82% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.95 (s, 0.16H), 7.60 (d, J = 7.6Hz, 1H), 7.53–7.45 (m, 2H), 7.38 (dd, J =8.6,7.4Hz,2H),7.29(ddd,J=8.1,2.6,1.1Hz,1H),7.20–7.14(m,1H),7.07–7.02(m,2H). 13 C NMR (100MHz, CDCl3) δ191.61–191.04(m),158.43,156.24,138.03,130.44,130.06,124.68,124.60,124.20,119.50,118.16.

[0033] Example 6, Preparation of Compound 2f

[0034] The method is the same as Example 1, except that the reaction is carried out for 48 hours to obtain a yellow oil 2f (78.80 mg, 99% yield, 90% D ratio by 1 H NMR) 1 H NMR (400MHz, CDCl3) δ9.87 (s, 0.09H), 7.14 (s, 2H), 3.94 (d, J = 3.3Hz, 9H). 13 C NMR (100MHz, CDCl3) δ191.00–190.36(m),153.64,143.65,131.67,131.64,131.60,106.73,60.95,56.26.

[0035] Example 7, Preparation of Compound 2g

[0036] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain 2g of yellow oil (61.10mg, 93% yield, 97% D ratio by 1 H NMR) 1 H NMR (400MHz, CDCl3) δ9.81 (s, 0.03H), 7.40 (dd, J=5.3, 1.7Hz, 2H), 6.97 (d, J=8.7Hz, 1H), 4.36–4.26 (m, 4H). 13C NMR (100MHz, CDCl3) δ190.73–190.10(m),149.25,143.94,130.52,124.19,118.33,117.78,64.71,64.04.

[0037] Example 8, Preparation of Compound 2h

[0038] The method is the same as in Example 1, except that the reaction takes 24 hours, and the yellow oil is 2h (10.80mg, 50% yield, 97% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.97 (s, 0.03H), 7.95–7.89 (m, 2H), 7.27–7.18 (m, 2H). 13 C NMR (100MHz, CDCl3) δ190.52–189.88(m),167.84,165.29,132.28,132.18,116.49,116.26.

[0039] Example 9, Preparation of Compound 2i

[0040] The method is the same as Example 1, except that the reaction is carried out for 6 hours to obtain yellow oil 2i (23.40 mg, 41% yield, 97% D ratio by 1 H NMR) 1 H NMR (400MHz, CDCl3) δ9.98 (s, 0.03H), 7.86 (s, 1H), 7.77 (d, J = 7.8Hz, 1H), 7.61 (d, J = 7.9Hz, 1H), 7.49 (dd, J = 8.3, 7.2Hz, 1H). 13 C NMR (100MHz, CDCl3) δ191.65–189.00(m),137.89–137.65(m),135.48,134.41,130.39,129.32,127.97.

[0041] Example 10, Preparation of Compound 2j

[0042] The method is the same as Example 1, except that the reaction takes 6 hours, and the yellow oil 2j (23.60 mg, 42% yield, 94% D ratio by 1 1H NMR). 1 H NMR (400MHz, CDCl3) δ9.99 (s, 0.05H), 7.86–7.81 (m, 2H), 7.52 (d, J = 8.4Hz, 2H).13 C NMR (100MHz, CDCl3) δ190.84–190.27(m),140.99,134.71–134.60(m),130.91,129.48.

[0043] Example 11, Preparation of Compound 2k

[0044] The method is the same as in Example 1, except that the reaction lasts for 12 hours, and the yellow oil 2k (25.50 mg, 34% yield, 92% D ratio by 1 1H NMR). 1 H NMR (400MHz, CDCl3) δ9.98 (s, 0.07H), 7.78–7.73 (m, 2H), 7.71–7.67 (m, 2H). 13 C NMR (100MHz, CDCl3) δ191.03–190.44(m),135.08–134.98(m),132.46,130.97.

[0045] Example 12, Preparation of Compound 21

[0046] The method is the same as in Example 1, except that the reaction takes 24 hours, and the yellow oil 21 (13.9 mg, 42% yield, 93% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.99 (s, 0.06H), 7.93 (s, 2H), 7.28 (d, J = 8.6Hz, 2H), 2.34 (s, 3H). 13 C NMR (100MHz, CDCl3) δ190.92–190.28(m),168.68,155.38,134.01–133.89(m),131.20,122.37,21.14.

[0047] Example 13, Preparation of Compound 2m

[0048] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a white solid 2m (22.3 mg, 49% yield, 92% D ratio by 1 H NMR). 1H NMR (400MHz, CDCl3) δ10.02(s,0.07H),8.21(d,J=7.3Hz,2H),7.98(d,J=8.6Hz,2H),7.67(t,J=7.5Hz,1H),7.57–7.50(m,2H),7.45–7.39(m,2H). 13 C NMR (100MHz, CDCl3) δ190.99–190.30(m),164.51,155.73,134.04,131.27,130.30,128.74,122.56.

[0049] Example 14, Preparation of Compound 2n

[0050] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a white solid (37.0 mg, 78% yield, 96% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.89 (s, 0.04H), 7.85 (d, J = 8.4Hz, 2H), 7.00 (d, J = 8.4Hz, 2H), 4.61 (d, J = 1.3Hz, 2H), 1.49 (s, 9H). 13 C NMR (100MHz, CDCl3) δ190.79–190.07(m),167.15,162.80,131.92,130.51,114.86,82.91,65.54,28.01.

[0051] Example 15, Preparation of Compound 2o

[0052] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a white solid 2o (47.8 mg, 73% yield, 97% D ratio by 1 H NMR) as white solid. 1 H NMR (400MHz, CDCl3) δ9.92 (s, 0.03H), 7.86 (d, J = 8.7Hz, 2H), 7.71 (d, J = 8.5Hz, 3H), 2.24 (s, 3H). 13 C NMR (100MHz, CDCl3) δ191.27–190.67(m),169.07,143.78,131.19,119.31,24.77.

[0053] Example 16, Preparation of Compound 2p

[0054] The method is the same as in Example 1, except that 30 mol% of triisopropylsilanethiol is used and the reaction is carried out for 24 hours to obtain a yellow oily 2p (48.70 mg, 99% yield, 91% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.87 (s, 0.08H), 7.85–7.79 (m, 2H), 6.98 (d, J = 8.6Hz, 2H), 6.39 (s, 1H). 13 C NMR (100MHz, CDCl3) δ191.31–191.00(m),191.00,161.68,132.55,129.74,116.04.

[0055] Example 17, Preparation of Compound 2q

[0056] The method is the same as Example 1, except that 30 mol% of triisopropylsilanethiol is used and the reaction is carried out for 36 hours to obtain a yellow oil 2q (42.20 mg, 68% yield, 87% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ10.14 (s, 0.12H), 8.31 (s, 1H), 8.01–7.86 (m, 4H), 7.60 (dddd, J = 22.8, 8.1, 6.9, 1.4Hz, 2H). 13 CNMR(100MHz,CDCl3)δ192.22–191.60(m),136.48,134.55,134.53,134.08( dd,J=7.6,4.0Hz),132.66,129.54,129.14,129.11,128.10,127.11,122.77.

[0057] Example 18, Preparation of Compound 2r

[0058] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a yellow oil 2r (61.90 mg, 85% yield, 90% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ10.04(s,0.09H),7.96–7.91(m,2H),7.75–7.71(m,2H),7.64–7.60(m,2H),7.49–7.44(m,2H),7.43–7.38(m,1H). 13C NMR (100MHz, CDCl3) δ191.85–191.21 (m), 147.20, 139.75, 135.21 (dd, J = 7.5, 4.0Hz), 130.26, 129.04, 128.49, 127.69, 127.38.

[0059] Example 19, Preparation of Compound 2s

[0060] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a yellow oil 2s (54.00 mg, 93% yield, 94% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ10.08 (s, 0.05H), 8.74 (s, 1H), 8.35–8.31 (m, 1H), 7.86 (d, J = 3.1Hz, 1H), 7.47–7.43 (m, 1H), 7.35–7.32 (m, 2H). 13 C NMR (100MHz, CDCl3) δ124.47,123.08,122.06,111.46.

[0061] Example 20, Preparation of Compound 2t

[0062] The method is the same as Example 1, except that the reaction takes 24 hours to obtain a yellow oil 2t (41.10 mg, 92% yield, 93% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ10.07(s,0.06H),8.58(s,1H),8.13(d,J=7.8Hz,1H),7.99(d,J=7.9Hz,1H),7.52(t ,J=7.3Hz,1H),7.44(d,J=8.1Hz,2H),7.31(t,J=7.4Hz,1H),4.37(q,J=7.3Hz,2H),1.44(t,J=7.2Hz,3H). 13 C NMR(100MHz, CDCl3)δ191.81–191.22(m),143.59,140.70,128.43,127.19,12 6.75,124.02,123.16,123.08,120.81,120.33,109.17,108.70,37.93,13.83.

[0063] Example 21, Preparation of Compound 2u

[0064] The method is the same as in Example 1, except that 13 mol% of triisopropylsilanethiol is used and the reaction is carried out for 36 hours to obtain a yellow oil 2u (18.3 mg, 68% yield, 89% D ratio by 1 H NMR) as white solid. 1 H NMR (400MHz, CDCl3) δ9.82 (s, 0.10H), 7.32–7.17 (m, 5H), 2.96 (t, J = 7.6Hz, 2H), 2.77 (t, J = 7.4Hz, 2H). 13 C NMR (100MHz, CDCl3) δ201.64–200.94(m),140.36,128.62,128.30,126.32,45.23–44.98(m),28.11.

[0065] Example 22, Preparation of Compound 2v

[0066] The method is the same as Example 1, except that the reaction takes 24 hours to obtain a yellow oil 2v (27.00 mg, 53% yield, 83% D ratio by 1 H NMR). 1 H NMR (400MHz, CDCl3) δ9.76(t,J=1.9Hz,0.11H),2.42(t,J=7.4Hz,2H),1.67–1.61(m,2H),1.29(dt,J=11.3,3.7Hz,8H),0.89(d,J=6.8Hz,3H). 13 C NMR (100MHz, CDCl3) δ202.95–202.28(m),43.90,43.80–43.65(m),31.61,29.13,29.00,22.57,22.07,14.05(d,J=6.8Hz).

[0067] Example 23, Preparation of Compound 2w

[0068] The method is the same as Example 1, except that the reaction is carried out for 24 hours to obtain a yellow oil 2w (58.60 mg, 79% yield, 92% D ratio by 1 H NMR). 1 HNMR (400MHz, CDCl3) δ9.76 (s, 0.07H), 2.41 (t, J = 7.4Hz, 2H), 1.28 (m, 18H), 0.88 (t, J = 6.7Hz, 4H). 13C NMR (100MHz, CDCl3) δ202.84–202.27(m),31.89,29.72–29.27(m),29.17,22.66,22.06,14.07.

[0069] Example 24, Preparation of Compound 2x

[0070] The method is the same as in Example 1, except that 15 mol% of triisopropylsilanethiol is used, and the reaction is carried out for 24 hours to obtain a yellow oil 2x (34.10 mg, 44% yield, 94% D ratio by 1 HNMR). 1 H NMR (400MHz, CDCl3) δ9.80 (s, 0.05H), 3.99 (t, J = 6.1Hz, 2H), 2.59 (t, J = 6.1Hz, 2H), 0.88 (s, 10H), 0.07 (s, 6H). 13 C NMR (100MHz, CDCl3) δ201.79,57.41,46.44,46.41,46.37,29.71,25.81,5.44.

[0071] Example 25, Preparation of Compound 2y

[0071] The method is the same as Example 1, except that 30 mol% of triisopropylsilanethiol is used. The reaction is carried out for 24 hours to obtain a yellow oil 2y (24.00 mg, 49% yield, 92% D ratio by 1 H NMR). 1 H NMR(400MHz, CDCl3)δ9.79(s,0.07H),6.24–6.20(m,1H),5.99(m,1H),3.25(s,1H),2.99 (s,1H),2.90(dt,J=8.1,3.9Hz,1H),1.93–1.87(m,1H),1.60(s,1H),1.51–1.43(m,2H). 13 C NMR (100MHz, CDCl3) δ204.11,137.12,130.79,51.22,48.62,44.01,41.73,28.69,28.65.

[0073] Example 26, Preparation of Compound 2z

[0074] The method is the same as Example 1, except that the reaction is carried out for 36 hours to obtain a yellow oil 2z (70.20 mg, 82% yield, 87% D ratio by 1H NMR). 1 H NMR (400MHz, CDCl3) δ9.66 (s, 0.12H), 3.98 (d, J = 13.7Hz, 2H), 3.01–2.87 (m, 2H), 2.41 (tt, J = 10 .5,4.0Hz,1H),1.89(dd,J=13.4,3.9Hz,2H),1.56(m,J=13.7,8.9,4.1Hz,2H),1.46(s,9H).13C NMR(100MHz, CDCl3)δ202.96–202.37(m),154.66,79.71,47.98–47.74(m),29.67,28.39.

[0075] The above-described embodiment is only a preferred solution of the present invention and does not limit the present invention in any form. There are other variations and modifications without exceeding the technical solution described in the claims.

Claims

1. A deuterated aldehyde compound as shown in formula I, characterized in that The hydrogen on the formyl group of the aldehyde is deuterium, an isotope of hydrogen, and its general structural formula is as follows: Among them: R 1 is aryl, substituted aryl, polycyclic aryl, heterocyclic aryl, substituted heterocyclic aryl, polycyclic aryl, C 1-18 Alkyl, C 1-10 Cycloalkyl.

2. The compound of formula I as claimed in claim 1 includes but is not limited to the following compounds:

3. The method for preparing the deuterated aldehyde compound according to claim 1-2, characterized in that The method comprises the following steps: Step 1: At room temperature, under an argon atmosphere, aldehyde (1, 0.2-0.4mmol, 1.0 equivalent), triisopropylsilanethiol (2.2uL, 5-30mol%), heavy water (160uL, 40equiv) and 1.0mL of anhydrous ethyl acetate are added to the reaction tube. The solution is degassed by freeze-pump-thaw and then plugged with a rubber stopper. The reaction solution is stirred for 6-48 hours under a 380nm LED. After the reaction is completed, the reaction solution is concentrated. In this step, the solvent can also be acetonitrile, acetone, 1,2-dichloroethane, dichloromethane, chloroform, ethyl acetate, methyl propionate, ethyl propionate, methyl formate, ethyl formate or a mixed solvent of two of them. However, ester solvents are preferred. In this step, the wavelength of the light used can be any wavelength or band from 365nm to 450nm. However, any wavelength or band from 380nm to 400nm is preferred. In this step, the thiol used includes triphenylsilane thiol, triisopropylsilane thiol and phenylethyl thiol, but triisopropylsilane thiol is preferred. The reaction tube can be made of glass or quartz, but quartz is preferred. Step 2: After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain the target compounds 2a-2z.

4. The deuterated aldehyde compounds can be used as synthetic building blocks for the synthesis of other deuterated compounds.

Images