40615-35-8

Basic information

• Product Name: 4,4'-dimethoxytrityl alcohol
• Synonyms: 4,4'-dimethoxytrityl alcohol;4-Methoxy-α-(4-methoxyphenyl)-α-phenylbenzenemethanol;Bis(4-methoxyphenyl)phenylmethanol;Phenylbis(4-methoxyphenyl)methanol;α,α-Bis(4-methoxyphenyl)benzenemethanol
• CAS NO: 40615-35-8
• Molecular Formula: C₂₁H₂₀O₃
• Molecular Weight: 320.3817
• EINECS: 255-001-0
• Mol File: 40615-35-8.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 488°Cat760mmHg
• Flash Point: 248.9°C
• Appearance: /
• Density: 1.151g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.87±0.29(Predicted)
• CAS DataBase Reference: 4,4'-dimethoxytrityl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-dimethoxytrityl alcohol(40615-35-8)
• EPA Substance Registry System: 4,4'-dimethoxytrityl alcohol(40615-35-8)

Safety Data

• Hazardous Substances Data: 40615-35-8(Hazardous Substances Data)

Usage

Description

4,4'-Dimethoxytrityl alcohol, also known as p,p''-Dimethoxytriphenylcarbinol, is an organic compound with the molecular formula C23H22O4. It is a colorless crystalline solid that is soluble in organic solvents. It is characterized by its trityl core with two methoxy groups attached to the para positions of the phenyl rings.

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 
• 67-56-1 methanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 103281-33-0 2,2-bis-(p-methoxyphenyl)-1,2-diphenylethanone 
• 14039-15-7 4,4'-dimethoxytrityl cation 
• 85562-05-6 C₈₇H₉₆N₁₀O₂₂P₂S₃ 
• 85562-06-7 C₁₄₇H₁₆₈N₂₀O₄₂P₄S₅ 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 100-58-3 phenylmagnesium bromide 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 120264-80-4 2,2-bis(4-methoxyphenyl)-2-phenylacetonitrile 
• 93966-67-7 benzoic acid [5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl] ester 
• 289681-49-8 1-[(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(1,1-dimethylethyl)diphenylsilyl]oxy}tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 
• 93966-64-4 3'-benzoyl-5'-O-(4,4'-dimethoxytrityl)thymidine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 

Relevant articles and documents

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.

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.

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.