154925-95-8

Basic information

• Product Name: 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine
• Synonyms: 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine;5-BroMo-2'-deoxy-3',5'-bis-O-[(1,1-diMethylethyl)diMethylsilyl]-uridine
• CAS NO: 154925-95-8
• Molecular Formula: C21H39BrN2O5Si2
• Molecular Weight: 535.61976
• Product Categories: Bases & Related Reagents;Heterocycles;Nucleotides;Heterocycles, Nucleotides, Bases & Related Reagents
• Mol File: 154925-95-8.mol

Chemical Properties

• Melting Point: 142-144°C
• Appearance: /
• Density: 1.212g/cm³
• Refractive Index: 1.514
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine(154925-95-8)
• EPA Substance Registry System: 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine(154925-95-8)

Safety Data

• Hazardous Substances Data: 154925-95-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine is used as an intermediate for the synthesis of cytidine derivatives, which are essential in the development of various pharmaceutical products. Its role in the synthesis process is crucial for creating compounds with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine is utilized for studying the properties and reactions of cytidine derivatives. This helps researchers understand the structure-activity relationships and potential applications of these compounds in various fields, including drug discovery and development.
Used in Biochemical Applications:
3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine may also be employed in biochemical applications, such as the study of nucleic acid interactions and the development of novel nucleotide analogs with specific biological activities. Its unique structure allows for the exploration of its interactions with enzymes, proteins, and other biomolecules, potentially leading to the discovery of new therapeutic agents.

InChI:InChI=1/C21H39BrN2O5Si2/c1-20(2,3)30(7,8)27-13-16-15(29-31(9,10)21(4,5)6)11-17(28-16)24-12-14(22)18(25)23-19(24)26/h12,15-17H,11,13H2,1-10H3,(H,23,25,26)/t15?,16-,17-/m1/s1

Upstream product

• 59-14-3 5-bromo-2'-deoxyuridine 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1429644-49-4 6-methyl-2'-deoxyuridine 
• 50-89-5 thymidine 

Relevant articles and documents

Enhanced H-bonding and π-stacking in DNA: A potent duplex-stabilizing and mismatch sensing nucleobase analogue

X-pyrene is a new nucleic acid duplex stabilizing cytosine analogue that combines enhanced π-stacking, hydrogen bonding and electrostatic interactions to greatly increase the stability of bulged DNA duplexes and DNA/RNA hybrids. X-pyrene is highly selective for guanine as a partner and duplex stability is reduced dramatically when X-pyrene or a neighboring base is mismatched. An NMR study indicates that the pyrene moiety stacks within the helix, and large changes in fluorescence emission on duplex formation are consistent with this. These favorable properties make X-pyrene a promising cytosine analogue for use in a variety of biological applications.

Selective alkylation of pyrimidyl dianions II: Synthesis, characterization, and comparative reactivity of 3′, 5′-o-bis- tetrahydropyranyl, trimethylsilyl and tert-butyldimethylsilyl derivatives of 5-bromo-2′-deoxyuridine

Three compounds which can be used as precursors for thymidine synthesis via methylation at the 5 position, including 3′, 5′-o-bis(tetrahydropyranyl)-5-bromo-2′-deoxyuridine 1a, 3′, 5′-o-bis-(trimethylsily)-5-bromo-2′-deoxyuridine 1b, and 3′, 5′-o-bis-(t-butyldimethylsilyl)-5-bromo-2′-deoxyuridine 1c, were prepared, isolated and characterized by spectroscopic methods. Alkylation with methyl iodide using an organo-lithium reagent at low temperature produced 72%, 41% and 74% of thymidine 6, respectively. Tetrahydropyranyl and t-butyldimethylsilyl ethers are found to be better precursors for introduction of a methyl group at the 5 position.

Synthesis of 5-Dihydroxyboryluridine Phosphoramidite and Its Site-Specific Incorporation into Oligonucleotides for Probing Thymine DNA Glycosylase

A concise synthetic strategy to 5-dihydroxyboryldexoyuridine (5boU) phosphoramidite has been developed. 5boU was introduced into short oligonucleotides in a site-specific manner, demonstrating compatibility of the boronic acid moiety with standard solid-phase DNA synthesis chemistry. Electrophilic 5boU DNAs inhibited thymine DNA glycosylase, a cancer-relevant DNA-modifying enzyme. We envisage diverse applications of 5boU in organic synthesis, medicinal chemistry, and chemical biology.

5-Modified-2'-dU and 2'-dC as mutagenic Anti HIV-1 proliferation agents: Synthesis and activity

With the goal of limiting HIV-I proliferation by increasing the mutation rate of the viral genome, we synthesized a series of pyrrolidine nucleoside analogues modified in position 5 of the aglycone moiety but unmodified on the sugar part. The synthetic strategies allow us to prepare the targeted compounds directly from commercially available nucleosides. All compounds were tested for their ability to reduce HIV-I. proliferation in cell culture. Two of them (5-hydroxymethyl-2'-dU (1c) and 5-hydroxymethyl-2'-dC (2c)) displayed a moderate antiviral activity in single passage experiments. The same two compounds plus two additional ones (5-carbamoyl-2'-dU (la) and 5-carbamoylmethyl-2'-dU (1b)) were potent, inhibitors of HIV-1 RT activity in serial passage assays, in which they induced a progressive loss of HIV-1 replication. In addition, viruses collected after seven passages in the presence of 1c and 2c replicated very poorly after withdrawal of these compounds, consistent with the accumulation of deleterious mutations in the HIV-1. genome.

Design and synthesis of thalidomide-deoxyribonucleoside chimeras

Novel thalidomide-deoxyribonucleoside chimeras have been synthesized as potentially safe, thalidomide-based antitumour agents. Copyright