40615-35-8

Usage

Uses

Used in Chemical Synthesis:
4,4'-Dimethoxytrityl alcohol is used as a reagent in the regioselective tritylation of sugar-based diols. This application is particularly relevant in the field of organic chemistry, where it aids in the protection of hydroxyl groups during synthetic reactions, preventing unwanted side reactions and facilitating the selective functionalization of specific sites on complex molecules.
Used in Amberlyst-15 Catalyzed Reactions:
In the context of Amberlyst-15 catalyzed reactions, 4,4'-dimethoxytrityl alcohol serves as a key reactant for the tritylation of sugar-based diols. Amberlyst-15 is a strongly acidic ion-exchange resin that acts as a catalyst in this process, enhancing the efficiency and selectivity of the tritylation reaction. This application is significant in the synthesis of various biologically active compounds and pharmaceuticals that contain sugar moieties.

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 623-12-1 4-chloromethoxybenzene 
• 112219-63-3 (4-methoxyphenyl)magnesium iodide 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 103281-33-0 2,2-bis-(p-methoxyphenyl)-1,2-diphenylethanone 
• 85562-06-7 C₁₄₇H₁₆₈N₂₀O₄₂P₄S₅ 
• 125016-87-7 bis(4-methoxyphenyl)phenylmethyl methyl ether 
• 98-88-4 benzoyl chloride 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 25726-04-9 phenylglyoxylyl chloride 
• 100-66-3 methoxybenzene 
• 611-73-4 Benzoylformic acid 
• 38460-95-6 undec-10-enoyl chloride 

Downstream Products

• 61137-70-0 (R)-2-Amino-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanyl]-propionic acid 
• 95625-93-7 bis(4-methoxyphenyl)phenylacetic acid 
• 664-35-7 Hydroxy-phenyl-bis-(4-hydroxy-phenyl)-methan 
• 263746-51-6 4,4'-dimethoxytriphenylmethanethiol 
• 153652-92-7 N-4,4'-dimethoxytritylazetidine 
• 153652-94-9 3-chloro-N-4,4'-dimethoxytritylpropanamine 
• 125016-87-7 bis(4-methoxyphenyl)phenylmethyl methyl ether 
• 1254223-76-1 (MeO)2Tr-OAc 
• 1277097-06-9 5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxyuridine 
• 1277097-07-0 C₅₅H₅₃N₃O₁₀ 
• 1277097-09-2 5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine 
• 1277097-10-5 N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine 
• 188411-06-5 N₄-benzoyl-5-(2-cyanoethyl)hydroxymethyl-5'-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-[N,N-diisopropyl-N-cyanoethyl]phosphoramidite 
• 23669-79-6 DMT-dU 

Relevant academic research and scientific papers

Characterization of a 5′-aldehyde terminus resulting from the oxidative attack at C5′ of a 2-deoxyribose on DNA

The 5′-aldehyde terminus is a DNA oxidative damage resulting from attack at C5′ of 2-deoxyriboses by some potent natural or chemical DNA cleavers. To offer a fast and specific method for characterization of this type of damage, we used on-line electrospray ionization mass spectrometry (ESI-MS) detection during liquid chromatography analyses. The intrinsic reactivity of 5′-aldehyde terminus with nucleophiles (formation of hydrate with water, of a Tris adduct with Tris buffer) or through β-elimination reaction resulted in complex LC profiles and MS data. We showed that derivatization of the aldehyde function as an oxime ether gives a stable derivative easy to characterize during on-line ESI-MS analyses. Complete structural characterization of the Tris adduct and the oxime ether derivative were obtained from MS and detailed NMR studies performed on derivatized 5′-aldehyde thymidine models.

Efficient separation and purification method of 4,4'-dimethoxytrityl chloride and 4,4'-dimethoxytrityl alcohol

The invention provides an efficient separation and purification method of 4,4'-dimethoxytrityl chloride and 4,4'-dimethoxytrityl alcohol. According to the method, a target product with high purity isprepared on the basis of ensuring high reaction yield, impurity components contained in the target product are clarified, the content of the impurity components is controlled, and particularly the content of hydroxyl impurities and the content of acetylated impurities are controlled to be 0.05% or less.

Synthesis method of high-purity 4, 4 '-dimethoxytriphenylchloromethane

The invention provides a synthesis method of high-purity 4, 4 '-dimethoxytriphenylchloromethane, which comprises the following steps: by using anisole and trichlorotoluene as initial raw materials, carrying out F-C reaction, hydrochloric acid hydrolysis reaction and chlorination reaction to prepare a DMT-Cl crude product of which the purity is higher than 98.5%, and carrying out solvent crystallization to obtain a DMT-Cl finished product of which the purity is higher than 99.9%, thereby obtaining the DMT-Cl finished product yield higher than 98%. According to the method provided by the invention, on the basis of ensuring high reaction yield, the target product is prepared with high purity, impurity components contained in the target product are clear, the content of the impurity componentsis controlled, and particularly, hydroxyl impurities and acetylated impurities are controlled to be 0.05% or below.

Biomimetic 2-Imino-Nazarov Cyclizations via Eneallene Aziridination

Amidoallyl cations are appealing three-carbon synthons for the preparation of complex amine-containing carbocycles; however, methods to generate and utilize these reactive species are limited and underexplored compared to those for oxallyl cations. Here we disclose a bioinspired strain-driven ring opening of bicyclic methyleneaziridines to 2-amidopentadienyl cation intermediates that readily engage in Nazarov cyclizations. Advantages of this strategy include ease of generation and improved reactivity compared to 3-pentadienyl cations, control over the ultimate position of the alkene, the potential for high dr between vicinal stereocenters, and the ability to further elaborate the products to fully substituted aminocyclopentanes. Experimental and computational studies support a dual role for the Rh2Ln complex as both a nitrene transfer catalyst and a Lewis acid promoter, insight that provides a framework for the future development of asymmetric 2-imino-Nazarov cyclizations.

Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates

Regioselective protection of primary hydroxyl group in nucleoside and carbohydrate analogs was accomplished using dimethoxytrityl alcohol (DMTr-OH) or dimethylpixyl alcohol (DMPx-OH) in presence of copper(II)nitrate as a Lewis acid catalyst. Excellent selectivity was observed for the protection of primary hydroxyl group over secondary while glycosidic bond remain unaffected. Utility of this methodology was further exemplified via DMTr- and DMPx-protection of alipahtic acyclic and cyclic diols.

Renewable amberlyst-15 catalyzed highly regioselective tritylation and deprotection of sugar-based diols

Amberlyst-15 catalyzed highly regioselective tritylation of sugar-based diols was achieved under mild condition using 4,4′-dimethoxytrityl alcohol (DMTrOH). Deprotection of the corresponding DMTr group was also established by the variation to protic solvent. Meanwhile, the heterogeneous catalyst Amberlyst-15 was recycled 3 times with satisfactory retention of catalytic activity and proved its potential application in industry.

Direct allylation of benzyl alcohols, diarylmethanols, and triarylmethanols mediated by XtalFluor-E

We report the direct allylation of benzyl alcohols, diarylmethanols and triarylmethanols mediated by XtalFluor-E using allyltrimethylsilane. The resulting allylated products are obtained in moderate to high yield.

Hydride Reduction by a Sodium Hydride-Iodide Composite

Sodium hydride (NaH) is widely used as a Br?nsted base in chemical synthesis and reacts with various Br?nsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.

Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry

An efficient method for the synthesis of ketones using organolithium and acid chlorides under continuous flow conditions has been developed. In contrast to standard batch chemistry, over-addition of the organolithium to the ketone for the formation of the undesired tertiary alcohol has been minimised representing a direct approach toward ketones.

MELANIN PRODUCTION INHIBITOR

Disclosed is a melanin production inhibitor which has an excellent inhibitory activity on the production of melanin and is highly safe. The melanin production inhibitor is represented by general formula (1) (excluding clotrimazole) and/or a pharmacologically acceptable salt thereof. In the formula, A1, A2 and A3 are independently selected from a hydrogen atom, an aryl group which may have a substituent, and an aromatic heterocyclic group which may have a substituent. At least one of A1, A2 and A3 is selected from the aryl group and the aromatic heterocyclic group, the total number of carbon atoms contained in A1, A2 and A3 is 6 to 50 and, when at least two of A1, A2 and A3 represent the aryl groups or the aromatic heterocyclic groups, the adjacent two aryl or aromatic heterocyclic groups may be bound to each other via an alkyl chain or an alkenyl chain to form a ring; m represents an integer of 0 to 2; X represents a hetero atom, a hydrogen atom, or a carbon atom; R1 and R2 are independently selected from a hydrogen atom and an oxo group. When one of R1 and R2 is an oxo group, the other is not present. R3 is selected from a hydrogen atom, and a C1-8 hydrocarbon group in which one or some of hydrogen atoms or carbon atoms may be substituted by a hetero atom or hetero atoms. The number of R3's present in the compound corresponds to X and, when two or more R3's are present, the R3's are independently present and the adjacent two R3's may be bound to each other to form, together with X, a ring, and the terminal of R3 may be bound to a carbon atom to which A1, A2 and A3 are bound, thereby forming a ring.