6161-23-5

Basic information

• Product Name: 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE
• Synonyms: 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE;5-BroMo-2'-deoxy-uridine 3',5'-Diacetate
• CAS NO: 6161-23-5
• Molecular Formula: C₁₃H₁₅BrN₂O₇
• Molecular Weight: 391.172
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 6161-23-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 148-150°C
• Appearance: /
• Density: 1.667g/cm³
• Refractive Index: 1.586
• Storage Temp.: Refrigerator
• PKA: 7.73±0.10(Predicted)
• CAS DataBase Reference: 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE(6161-23-5)
• EPA Substance Registry System: 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE(6161-23-5)

Safety Data

• Hazardous Substances Data: 6161-23-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

3’, 5’-Di-O-acetyl-5-bromo-2’-deoxyuridine (cas# 6161-23-5) is a compound useful in organic synthesis.

InChI:InChI=1/C13H15BrN2O7/c1-6(17)21-5-10-9(22-7(2)18)3-11(23-10)16-4-8(14)12(19)15-13(16)20/h4,9-11H,3,5H2,1-2H3,(H,15,19,20)/t9-,10-,11-/m1/s1

Upstream product

• 13030-62-1 3',5'-di-O-acetyl-2'-deoxyuridine 
• 108-24-7 acetic anhydride 
• 59-14-3 5-bromo-2'-deoxyuridine 

Downstream Products

• 59-14-3 5-bromo-2'-deoxyuridine 
• 1332507-70-6 3',5'-di-O-tert-butyldimethylsilyl-N-[4-(2-N-benzylcarbamylethoxy-4,6-O-tert-butyldimethylsilylphenyl)]-2'-deoxy-5-bromouridine 
• 1332507-56-8 3-(3',5'-di-O-tert-butyldimethylsilyl-d-ribofuranosyl)-9-(2-N-benzylcarbamylethoxy)-1,3-diaza-7-O-tert-butyldimethylsilyl-2-oxophenoxadine 
• 1332507-57-9 3-(3',5'-di-O-tert-butyldimethylsilyl-d-ribofuranosyl)-9-(2-N-benzylcarbamylethoxy)-1,3-diaza-7-hydroxy-2-oxophenoxadine 
• 1332507-58-0 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-trifluoromethylsulfonyl-2-oxophenoxadine 
• 1332507-59-1 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-phenyl-2-oxophenoxadine 
• 1332507-60-4 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-(1-naphthyl)-2-oxophenoxadine 
• 1332507-61-5 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-(4-methoxyphenyl)-2-oxophenoxadine 
• 1332507-62-6 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-(4-cyanophenyl)-2-oxophenoxadine 
• 1332507-63-7 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-(thiophenyl-2-yl)-2-oxophenoxadine 

Relevant articles and documents

Why does the type of halogen atom matter for the radiosensitizing properties of 5-halogen substituted 4-thio-20-deoxyuridines?

Radiosensitizing properties of substituted uridines are of great importance for radiotherapy. Very recently, we confirmed 5-iodo-4-thio-20-deoxyuridine (ISdU) as an efficient agent, increasing the extent of tumor cell killing with ionizing radiation. To our surprise, a similar derivative of 4-thio-2’-deoxyuridine, 5-bromo-4-thio-20-deoxyuridine (BrSdU), does not show radiosensitizing properties at all. In order to explain this remarkable difference, we carried out a radiolytic (stationary and pulse) and quantum chemical studies, which allowed the pathways to all radioproducts to be rationalized. In contrast to ISdU solutions, where radiolysis leads to 4-thio-2’-deoxyuridine and its dimer, no dissociative electron attachment (DEA) products were observed for BrSdU. This observation seems to explain the lack of radiosensitizing properties of BrSdU since the efficient formation of the uridine-5-yl radical, induced by electron attachment to the modified nucleoside, is suggested to be an indispensable attribute of radiosensitizing uridines. A larger activation barrier for DEA in BrSdU, as compared to ISdU, is probably responsible for the closure of DEA channel in the former system. Indeed, besides DEA, the XSdU anions may undergo competitive protonation, which makes the release of X? kinetically forbidden.

Functionalized tricyclic cytosine analogues provide nucleoside fluorophores with improved photophysical properties and a range of solvent sensitivities

Tricyclic cytosines (tC and tCO frameworks) have emerged as a unique class of fluorescent nucleobase analogues that minimally perturb the structure of B-form DNA and that are not quenched in duplex nucleic acids. Systematic derivatization of th

Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin

Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5-dimethylhydantoin in aprotic solvents such as CH 2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination.