82444-76-6

Basic information

• Product Name: 2',3'-Bis-O-(t-butyldiMethylsilyl)-5'-O-(4,4'-diMethyltriphenylMethyl)uridine
• Synonyms: 2',3'-Bis-O-(t-butyldiMethylsilyl)-5'-O-(4,4'-diMethyltriphenylMethyl)uridine
• CAS NO: 82444-76-6
• Molecular Formula: C42H58N2O8Si2
• Molecular Weight: 743.09072
• Mol File: 82444-76-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2',3'-Bis-O-(t-butyldiMethylsilyl)-5'-O-(4,4'-diMethyltriphenylMethyl)uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-Bis-O-(t-butyldiMethylsilyl)-5'-O-(4,4'-diMethyltriphenylMethyl)uridine(82444-76-6)
• EPA Substance Registry System: 2',3'-Bis-O-(t-butyldiMethylsilyl)-5'-O-(4,4'-diMethyltriphenylMethyl)uridine(82444-76-6)

Safety Data

• Hazardous Substances Data: 82444-76-6(Hazardous Substances Data)

Usage

General Description

2',3'-Bis-O-(t-butyldiMethylsilyl)-5'-O-(4,4'-diMethyltriphenylMethyl)uridine is a synthetic chemical compound commonly used in organic chemistry research. It is a derivative of uridine, a nucleoside that is found in RNA molecules. The compound is often used in the synthesis of nucleic acid analogs and prodrugs. The t-butyldimethylsilyl (TBDMS) and 4,4'-dimethyltriphenylmethyl (DMT) groups are protective groups, which help to prevent unwanted reactions during the synthesis process. These protective groups can be easily removed under mild conditions, allowing the uridine derivative to be used in further reactions. The compound is valuable in the development of new pharmaceuticals, and its unique structure makes it a useful tool for understanding the chemical and biological properties of nucleosides.

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 58-96-8 uridine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 81246-79-9 5'-dimethoxytrityluridine 

Downstream Products

• 82456-21-1 4-hydrazino-1-<5'-O-(dimethoxytrityl)-2',3'-O-bis(tert-butyldimetylsilyl)-β-D-ribofuranosyl>pyrimidin-2(1H)-one 
• 82444-79-9 5'-O-(dimethoxytrityl)-2',3'-O-bis(tert-butyldimetylsilyl)-N⁴,N⁴-dimethylcytidine 
• 82444-78-8 5'-O-(dimethoxytrityl)-2',3'-O-bis(tert-butyldimetylsilyl)-N⁴-methylcytidine 
• 82444-77-7 5'-O-(dimethoxytrityl)-2',3'-O-bis(tert-butyldimetylsilyl)cytidine 
• 137330-29-1 C₄₂H₇₁N₃O₁₄Si₂ 
• 137233-58-0 C₄₂H₇₁N₃O₁₄Si₂ 
• 137233-51-3 C₅₀H₇₉N₃O₁₄SeSi₃ 
• 137233-57-9 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine 
• 137233-53-5 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine-5'-aldehyde 
• 82456-20-0 1-(5'-O-(dimethoxytrityl)-2',3'-bis(tert-butyldimetylsilyl)-β-D-ribofuranosyl)-4-(1,2,4-triazol-1-yl)-pyrimidin-2-(1H)-one 

Relevant articles and documents

5’-Phosphorylation Increases the Efficacy of Nucleoside Inhibitors of the DNA Repair Enzyme SNM1A

Certain cancers exhibit upregulation of DNA interstrand crosslink repair pathways, which contributes to resistance to crosslinking chemotherapy drugs and poor prognoses. Inhibition of enzymes implicated in interstrand crosslink repair is therefore a promising strategy for improving the efficacy of cancer treatment. One such target enzyme is SNM1A, a zinc co-ordinating 5’–3’ exonuclease. Previous studies have demonstrated the feasibility of inhibiting SNM1A using modified nucleosides appended with zinc-binding groups. In this work, we sought to develop more effective SNM1A inhibitors by exploiting interactions with the phosphate-binding pocket adjacent to the enzyme's active site, in addition to the catalytic zinc ions. A series of nucleoside derivatives bearing phosphate moieties at the 5’-position, as well as zinc-binding groups at the 3’-position, were prepared and tested in gel-electrophoresis and real-time fluorescence assays. As well as investigating novel zinc-binding groups, we found that incorporation of a 5’-phosphate dramatically increased the potency of the inhibitors.

Synthetic studies of the tunicamycin antibiotics. Preparation of (+)-tunicaminyluracil, (+)-tunicamycin-V, and 5′-epi-tunicamycin-V

A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.