N-Benzoyl-2'-O-methoxyethyl-5-O-dimethoxytrityl-5-methylcytidine
[CAS# 182496-01-1]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleoside intermediate
• Name: N-Benzoyl-2'-O-methoxyethyl-5-O-dimethoxytrityl-5-methylcytidine
• Synonyms: N-Benzoyl-5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-(2-methoxyethyl)-5-methylcytidine
• Molecular Formula: C₄₁H₄₃N₃O₉
• Molecular Weight: 721.79
• CAS Registry Number: 182496-01-1
• EC Number: 805-197-4
• SMILES: CC1=CN(C(=O)N=C1NC(=O)C2=CC=CC=C2)[C@H]3[C@@H]([C@@H]([C@H](O3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)O)OCCOC

Properties

• Density: 1.26

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

N-Benzoyl-2'-O-methoxyethyl-5-O-dimethoxytrityl-5-methylcytidine, commonly abbreviated N-Bz-2'-O-ME-5-OTD-5-MeC, is a complex nucleoside analog noted for its enhanced stability and utility in nucleic acid chemistry. The compound embodies advances in nucleoside modification aimed at improving the performance and functionality of nucleoside-based research tools and therapeutics.

The synthesis of N-Bz-2'-O-ME-5-OTD-5-MeC was prompted by the need to create nucleoside analogs with superior stability and handling properties. By incorporating a benzoyl group at the N-position of cytidine, a 2'-O-methoxyethyl group on the ribose sugar, and a 5-O-dimethoxytrityl (DMT) group at the 5' position, the researchers aimed to design a nucleoside with enhanced protection against degradation and increased versatility for use in a variety of applications.

The benzoyl group provides steric protection at the N position, while the 2'-O-methoxyethyl modification enhances stability against hydrolysis. The DMT group acts as a temporary protecting group for the 5'-hydroxyl group, allowing controlled manipulation during synthesis.

N-Bz-2'-O-ME-5-OTD-5-MeC is primarily used to synthesize nucleic acid sequences, including oligonucleotides and other nucleic acid constructs. The DMT group protects the 5'-hydroxyl group, facilitating efficient phosphoramidite chemistry in automated DNA and RNA synthesis. The 2'-O-methoxyethyl modification enhances the stability of synthetic nucleic acids, making them more robust and less susceptible to degradation.

In RNA research, this modified cytidine analog helps study RNA stability and function. The enhanced stability provided by the 2'-O-methoxyethyl group makes it a valuable tool for constructing stable RNA molecules, which is essential for understanding RNA folding, interactions, and function in cellular processes.

The stability and protection provided by N-Bz-2'-O-ME-5-OTD-5-MeC make it potential in drug development. Modification of this compound allows the creation of nucleoside analogs with improved pharmacokinetic properties that can be used to design novel therapeutics. These nucleoside analogs may have applications in the treatment of viral infections, cancer, and genetic diseases.