100898-63-3

Basic information

• Product Name: 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE
• Synonyms: DMT-NAC-DC;N4-ACETYL-5'-(DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE;N-ACETYL-5'-DMT DEOXYCYTIDINE;N4-Acetyl-2'-deoxy-5'-O-DMT-D-cytidine;N4-Acetyl-5''-O-(4,4''-dimethoxytrityl)-2''-deoxycytidine;5''-O-(4,4''-Dimethoxytrityl)-N4-acetyl-2''-deoxycytidine (synthetic);DMT-Ac-dC;N4-Acetyl-2'-deoxy-5'-O-DMT-cytidine
• CAS NO: 100898-63-3
• Molecular Formula: C₃₂H₃₃N₃O₇
• Molecular Weight: 571.62
• EINECS: 2017-001-1
• Mol File: 100898-63-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• Storage Temp.: Store dry at 2-8°C
• PKA: 10.28±0.20(Predicted)
• CAS DataBase Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE(100898-63-3)
• EPA Substance Registry System: 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ACETYL-2'-DEOXYCYTIDINE(100898-63-3)

Safety Data

• Hazardous Substances Data: 100898-63-3(Hazardous Substances Data)

Usage

General Description

5'-O-(4,4'-dimethoxytrityl)-N4-acetyl-2'-deoxycytidine is a chemical compound commonly used in the synthesis of nucleoside analogs for pharmaceutical purposes. It is a derivative of cytidine, a nucleoside composed of the nucleobase cytosine and the sugar ribose. The "5'-O-(4,4'-dimethoxytrityl)" group is a protective group commonly used in organic synthesis to protect hydroxyl groups, while the "N4-acetyl" group adds an acetyl group to the nitrogen atom on the fourth position of the cytosine ring. These modifications are often used to enhance the properties of nucleoside analogs, making them more stable and effective for use in various medications and pharmaceutical applications.

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

• 1089723-13-6 C₄₃H₄₅N₄O₈P 
• 256955-34-7 Acetic acid (2R,3S,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 76512-82-8 5'-O-(4,4'-dimethoxytrityl)deoxycytidine 
• 157543-67-4 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite 

Relevant articles and documents

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.

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.