817623-11-3

Basic information

• Product Name: 5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine
• Synonyms: 5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine
• CAS NO: 817623-11-3
• Molecular Formula: C31H30N2O7
• Molecular Weight: 542.588
• Mol File: 817623-11-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine(817623-11-3)
• EPA Substance Registry System: 5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine(817623-11-3)

Safety Data

• Hazardous Substances Data: 817623-11-3(Hazardous Substances Data)

Usage

General Description

5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine is a chemical compound commonly used in the field of organic chemistry and biochemistry. It is a derivative of uridine, a naturally occurring nucleoside that is a component of RNA. 5'-O-(4,4'-Dimethoxytrityl)-5-methyl-2,2'-anhydro-D-uridine is often used as a building block in the synthesis of nucleic acids and nucleoside analogs. Its specific structure, with a 5'-O-(4,4'-Dimethoxytrityl) protecting group and a 5-methyl-2,2'-anhydro modification, makes it useful for selective chemical reactions and for modifying the properties of nucleosides. Its applications range from biochemical research to pharmaceutical development, making it a valuable tool in the study and manipulation of nucleic acids.

Upstream product

• 22423-26-3 O-2,2'-cyclo-5-methyluridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 65-71-4 thymin 
• 1463-10-1 5-Methyluridine 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 

Downstream Products

• 153631-19-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-5-methyluridine 
• 930279-61-1 2'-methylseleno-5'-O-(4,4'-dimethoxytrityl)-5-methyluridine 
• 1198293-47-8 2'-deoxy-2'-methyltellanyl-5'-O-(4,4'-dimethoxytrityl)thymidine 
• 1025399-01-2 2'-deoxy-2'-phenyltellanyl-5'-O-(4,4'-dimethoxytrityl)thymidine 
• 212061-57-9 2'-O-(2-Hydroxyethyl)-5'-O-dimethoxytrityl-5-methyluridine 
• 242147-79-1 2'-O-[2-(amino)ethyl]-5'-O-(4,4'-dimethoxytrityl)-5-methyluridine 
• 1263796-39-9 C₃₃H₃₅N₅O₈ 
• 1263796-38-8 C₃₄H₃₈N₂O₁₁S 
• 1412707-61-9 2'-O-{2-[3-(7,8-didehydro-1,2:5,6-dibenzocyclooctynyl)oxyamido]ethyl}-5'-O-(4,4'-dimethoxytrityl)-5-methyluridine 
• 1412707-66-4 2'-O-{2-[3-(7,8-didehydro-1,2:5,6-dibenzocyclooctynyl)oxyamido]ethyl}-5'-O-(4,4'-dimethoxytrityl)-5-methyluridine 3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 1055036-95-7 C₄₈H₅₄N₅O₁₇P 
• 55486-09-4 2'-O-Methyl-5-methyluridine 

Relevant articles and documents

New preparation method for modified nucleoside 5'-DMTr-2'-EOE-thymidine

The invention relates to a new preparation method of a modified nucleoside, 5'-DMTr-2'-EOE-thymidine; in the method, borate, modified by a specified target group, serves as a source of an alkylation group of saccharides ring hydroxyl groups and Cs2CO3 serves as a catalyst, so that by performing a reaction with 5'-DMTr protected dehydrated thymidine, the target product, 5'-DMTr-2'-EOE-thymidine, can be produced at high yield and high selectivity. The method can easily and economically mass-synthesize the 5'-DMTr-2'-EOE-thymidine.

New telluride-mediated elimination for novel synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides

(Chemical Equation Presented) Several 2′,3′-dideoxynucleosides (ddNs) and 2′,3′-didehydro-2′,3′-dideoxynucleosides (d4Ns) are FDA-approved anti-HIV drugs. Via conveniently synthesized 2,2′-anhydronucleosides, we have developed a novel synthesis of d4Ns by discovering and applying a new telluride-mediated elimination reaction. Our experiment results show that after substitution of 2,2′-anhydronucleosides with a telluride monoanion, a telluride intermediate is formed, and its elimination leads to formation of the olefin products (d4Ns). Our mechanistic study indicates that this telluride-assisted reaction consists of two steps: substitution (or addition) and elimination. By using dimethyl ditelluride (0.1 equiv) as the reagent, d4Ns can be synthesized with yields up to 90% via this telluride-mediated elimination. Our novel strategy has great potential to simplify synthesis of these drugs and to further reduce cost of AIDS treatment and will also facilitate development of novel d4N and ddN analogues.

Compounds and oligomeric compounds comprising novel nucleobases

The present invention relates to nucleoside compositions comprising novel nucleobases and oligomeric compounds comprising at least one such nucleoside. These oligomeric compounds typically have enhanced binding affinity properties compared to oligomeric compounds without the modification. The oligomeric compounds are useful, for example, for investigative and therapeutic purposes.