100898-63-3

Usage

Uses

Used in Pharmaceutical Synthesis:
5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE is used as an intermediate in the synthesis of nucleoside analogs for pharmaceutical purposes. Its protective and acetylated groups enhance the stability and effectiveness of the resulting nucleoside analogs, making them suitable for use in various medications.
Used in Medication Development:
In the pharmaceutical industry, 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE is used as a building block for the development of new medications. Its unique structure allows for the creation of nucleoside analogs with improved properties, such as increased stability and targeted activity against specific diseases.
Used in Organic Synthesis:
5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE is used as a reagent in organic synthesis, particularly for the protection of hydroxyl groups during chemical reactions. The "5'-O-(4,4'-dimethoxytrityl)" group provides a temporary shield that can be removed once the desired reaction is complete, allowing for further modification or use of the nucleoside analog.
Used in Research and Development:
In the field of research and development, 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE is used as a tool for studying the properties and potential applications of nucleoside analogs. Its unique structure and modifications provide insights into the design and synthesis of new compounds with therapeutic potential.
Used in Drug Delivery Systems:
5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE can be used in the development of drug delivery systems, where its protective and acetylated groups may enhance the stability and targeted delivery of nucleoside analogs to specific cells or tissues, improving the therapeutic efficacy and reducing side effects.

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 32909-05-0 N⁴-acetyl-2'-deoxycytidine 
• 40615-35-8 4,4'-dimethoxytrityl alcohol 
• 951-77-9 2'-Deoxycytidine 

Downstream Products

• 76512-82-8 5'-O-(4,4'-dimethoxytrityl)deoxycytidine 
• 1133388-17-6 C₄₄H₄₇N₄O₈P 
• 1133388-21-2 C₄₄H₄₇N₄O₈P 

Relevant academic research and scientific papers

Tritylation of alcohols under mild conditions without using silver salts

Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was also tested on four nucleoside derivatives that have primary alcohols. Satisfactory results were also obtained.

Ultrafast cleavage and deprotection of oligonucleotides synthesis and use of C(Ac) derivatives

We have investigated the use of alkylamines as fast cleavage and deprotection reagents for the solid phase synthesis of oligonucleotides and found methylamine/ammonium hydroxide (or methylamine) as an efficient reagent. The transamination side product formed with the commonly used dC(b2) has been eliminated by the use of dC(Ac) phosphoramidite. This system has successfully been used in the synthesis of oligonucleotides and oligonucleoside phosphorothioates. DMT dC(Ac) hydrogen phosphonate and DMT ribo C(Ac)-2'-OMe phosphoramidite also have been prepared and used in the synthesis of oligonucleotides.

Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5'-hydroxyls for the syntheses of novel potential anticancer agents

Contrary to expectations, many primary hydroxy groups are completely unreactive in glycosylation reactions, or give the desired glycosides in very low yields accompanied by products of many side reactions. Hydrogens of such primary hydroxyls are shown to be intramolecularly hydrogen bonded. Intermediates formed by nucleophilic attack by these hydroxyls on activated glycosylating agents may resist hydrogen abstraction. This resistance to proton loss is postulated to be the origin of the observed unreactivity. It is shown that successful glycosylations take place under acidic conditions under which such hydrogen bonds cease to exist. Accordingly, direct galactosylations of the normally unreactive 5'-hydroxyls of nucleosides were accomplished for the first time with a galactose trichloroacetimidate donor in chloroform under silver triflate promotion. It is noted that such galactosylated anticancer nucleosides may have improved biological specificity. Contrary to expectations, many primary hydroxy groups are completely unreactive in glycosylation reactions, or give the desired glycosides in very low yields accompanied by products of many side reactions. Hydrogens of such primary hydroxyls are shown to be intramolecularly hydrogen bonded. Intermediates formed by nucleophilic attack by these hydroxyls on activated glycosylating agents may resist hydrogen abstraction. This resistance to proton loss is postulated to be the origin of the observed unreactivity. It is shown that successful glycosylations take place under acidic conditions under which such hydrogen bonds cease to exist. Accordingly, direct galactosylations of the normally unreactive 5′-hydroxyls of nucleosides were accomplished for the first time with a galactose trichloroacetimidate donor in chloroform under silver triflate promotion. It is noted that such galactosylated anticancer nucleosides may have improved biological specificity.

Fast Cleavage and Deprotection of Oligonucleotides

We have developed methylamine/ammonia as a fast cleavage and deprotection reagent which effects complete cleavage of oligonucleotides from the solid support in 5 min at room temperature and complete deprotection in 5 min at 65 deg C.The problem of transamination side products formation, faced with the commonly used dCbz (10percent side product) upon treatment with methylamine/ammonia, has been sucessfully solved by the use of dCac (0.0percent side product).DMT dCac phosphoramidite-methylamine/ammonia system furnished oligonucleotides in equal or superior quality as compared to the other systems.