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
• Article Data: 5

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

Chemical Properties

White to Off-White Solid

Uses

An intermediate in the preparation of cytidine derivatives

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

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

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.

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.

Design and synthesis of thalidomide-deoxyribonucleoside chimeras

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