64911-18-8

Basic information

• Product Name: 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine
• Synonyms: 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine;2'-Deoxy-3',5'-bis-O-[(1,1-diMethylethyl)diMethylsilyl]uridine
• CAS NO: 64911-18-8
• Molecular Formula: C₂₁H₄₀N₂O₅Si₂
• Molecular Weight: 456.7237
• Product Categories: Bases & Related Reagents;Heterocycles;Intermediates;Nucleotides
• Mol File: 64911-18-8.mol

Chemical Properties

• Appearance: /
• Density: 1.065g/cm³
• Refractive Index: 1.497
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine(64911-18-8)
• EPA Substance Registry System: 3',5'-Bis-O-(tert-butyldimethylsilyl)-2’-deoxyuridine(64911-18-8)

Safety Data

• Hazardous Substances Data: 64911-18-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C21H40N2O5Si2/c1-20(2,3)29(7,8)26-14-16-15(28-30(9,10)21(4,5)6)13-18(27-16)23-12-11-17(24)22-19(23)25/h11-12,15-16,18H,13-14H2,1-10H3,(H,22,24,25)/t15?,16-,18-/m1/s1

Upstream product

• 41251-37-0 methyl-d3-magnesium iodide 
• 148134-86-5 2'-deoxy-3',5'-bis(O-tert-butyldimethylsilyl)-5-iodouridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 76223-04-6 1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 32294-60-3 diphenyl ditelluride 

Downstream Products

• 124667-80-7 5-Benzylsulfanyl-1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 124667-81-8 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(4-methoxy-benzylsulfanyl)-1H-pyrimidine-2,4-dione 
• 213037-77-5 4-({1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hydroxy-methyl)-benzonitrile 
• 223638-08-2 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-1H-pyrimidine-2,4-dione 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 951-78-0 2'-deoxyuridine 
• 65-71-4 thymin 
• 3328-20-9 5-acetoxy-1H-pyrimidine-2,4-dione 
• 1252056-70-4 C₂₃H₄₂N₂O₇Si₂ 
• 213769-47-2 N₄-benzoyl-2'-deoxycytidine 
• 951-77-9 2'-Deoxycytidine 
• 93170-53-7 C₆₅H₁₀₀N₈O₉Si₄ 
• 93170-54-8 C₆₄H₉₈N₈O₈Si₄ 
• 93193-93-2 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-{2-[9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-(trityl-amino)-9H-purin-6-yloxy]-ethylamino}-1H-pyrimidin-2-one 

Relevant articles and documents

Deamination, oxidation, and C-C bond cleavage reactivity of 5-hydroxymethylcytosine, 5-formylcytosine, and 5-carboxycytosine

Three new cytosine derived DNA modifications, 5-hydroxymethyl-2′- deoxycytidine (hmdC), 5-formyl-2′-deoxycytidine (fdC) and 5-carboxy-2′-deoxycytidine (cadC) were recently discovered in mammalian DNA, particularly in stem cell DNA. Their function is currently not clear, but it is assumed that in stem cells they might be intermediates of an active demethylation process. This process may involve base excision repair, C-C bond cleaving reactions or deamination of hmdC to 5-hydroxymethyl-2′- deoxyuridine (hmdU). Here we report chemical studies that enlighten the chemical reactivity of the new cytosine nucleobases. We investigated their sensitivity toward oxidation and deamination and we studied the C-C bond cleaving reactivity of hmdC, fdC, and cadC in the absence and presence of thiols as biologically relevant (organo)catalysts. We show that hmdC is in comparison to mdC rapidly oxidized to fdC already in the presence of air. In contrast, deamination reactions were found to occur only to a minor extent. The C-C bond cleavage reactions require the presence of high concentration of thiols and are acid catalyzed. While hmdC dehydroxymethylates very slowly, fdC and especially cadC react considerably faster to dC. Thiols are active site residues in many DNA modifiying enzymes indicating that such enzymes could play a role in an alternative active DNA demethylation mechanism via deformylation of fdC or decarboxylation of cadC. Quantum-chemical calculations support the catalytic influence of a thiol on the C-C bond cleavage.

Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization

We report here the first synthesis of 5-phenyl-telluride-thymidine derivatives and the Te-phosphoramidite. We also report here the synthesis, structure and STM current-imaging studies of DNA oligonucleotides containing the nucleobases (thymine) derivatize

NOVEL COMPOUNDS AND DERIVATIZATION OF DNAS AND RNAS ON THE NUCLEOBASES OF PYRIMIDINES FOR FUNCTION, STRUCTURE, AND THERAPEUTICS

Disclosed are compounds of formula (I)3 a derivative, or a tautomer thereof, or a pharmaceutically acceptable salt of said compound or said tautomer. Also disclosed are methods of preparing compound of formula (I), a derivative, or a tautomer thereof, or

Protecting groups transfer: Unusual method of removal of tr and TBDMS groups by transetherification

The triphenylmethyl (Tr) group undergoes a transfer (transetherification or disproportionation) between the molecules of 5'-O-Tr-2'-deoxynucleosides in a process mediated by anhydrous sulfates of Cu+2, Fe+2, or Ni+2 to yield mixtures of 3',5'-bis-O-Tr and 3'-O-Tr products. If phenylmethanol is present in a reaction medium, detritylation results with concomitant formation of phenylmethyl triphenylmethyl ether. The behavior of t-butyldimethylsilyl (TBDMS) group in 5'-O-TBDMS-2'-deoxynucleosides is exactly the same. Such type of transetherifications was not observed before for the O-Tr and O-TBDMS groups. Copyright Taylor & Francis Group, LLC.