40733-27-5

Basic information

• Product Name: 3'-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE
• Synonyms: 3'-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE;3'-O-(TBDMS)THYMIDINE;3'-O-(tert-ButyldiMethylsilyl)thyMidine;3'-O-tert-butyldiMethylsilyl-2'-deoxythyMidine;3'-O-t-BulyldiMethylsilyl thyMidine;1-((2R,4S,5R)-4-((tert-Butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 40733-27-5
• Molecular Formula: C₁₆H₂₈N₂O₅Si
• Molecular Weight: 356.49
• Mol File: 40733-27-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 93-94 °C
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 3'-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE(40733-27-5)
• EPA Substance Registry System: 3'-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE(40733-27-5)

Safety Data

• Hazardous Substances Data: 40733-27-5(Hazardous Substances Data)

Usage

Description

3'-O-[tert-Butyl(dimethyl)silyl]thymidine is a nucleoside analog that is chemically stable and has been shown to be a potential biomarker for the diagnosis of fetal bovine spongiform encephalopathy (BSE). 3'-O-t-Bulyldimethylsilyl thymidine binds to basic proteins in the cell nucleus and has been shown to inhibit protein synthesis in tubule cells of the kidney and skin cancer cells.

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 40733-28-6 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 

Downstream Products

• 103022-81-7 C₄₇H₅₉N₄O₁₂PSi 
• 108691-17-4 C₄₉H₆₁N₄O₁₃PSi 
• 115244-24-1 C₅₄H₆₃N₄O₁₄PSi 
• 129801-99-6 3'-O-(tert-butyldimethylsilyl)-5'-O-(p-toluenesulfonyl)thymidine 
• 143331-47-9 Benzyl-phosphonic acid bis-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester 
• 143331-46-8 Isopropyl-phosphonic acid bis-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester 
• 143331-51-5 ((S)-2-Methyl-butyl)-phosphonic acid bis-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 143331-48-0 ((S)-2-Methyl-butyl)-phosphonic acid bis-[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester 
• 143331-50-4 Benzyl-phosphonic acid bis-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 145550-46-5 Phosphoric acid (2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester bis-(2-chloro-phenyl) ester 
• 1053299-82-3 C₄₈H₆₀N₄O₁₂Si 
• 133471-17-7 (R_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 133471-17-7 (S_P)-5'-O-(4,4-dimethoxytrityl)-2'-thymidylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 134407-75-3 O-(3'-O-t-butyldimethylsilylthymidin-5'-yl) O-(5'-dimethoxytritylthymidin-3'-yl) S-methyl thiophosphite 

Relevant articles and documents

A Practical Method for Regioselective 5′-O-tert-Butyldimethylsilyl Deprotection of Persilylated Nucleosides by Methanolic Phosphomolybdic Acid

In nucleoside/nucleotide chemistry, the regioselective cleavage of 5′-O-TBS groups of persilylated nucleosides is a desired approach for structural functionalization at the 5′-position. However, efficient and practical methods for this purpose are still limited. In our research, we found that homogeneous methanolic phosphomolybdic acid (PMA) efficiently catalyzes the regioselective deprotection of 5′- O -TBS groups of a diversity of persilylated nucleoside substrates and can be applied in practical synthesis at scales of up to 15 g. 31 P NMR results indicated that an anion cluster forms and the Lewis acidity of homogeneous PMA is organic-solvent dependent. The efficacy and pronounced regioselectivity of methanolic PMA occurs as a result of a lowering of the Lewis acid strength upon solvation of the molybdophosphate anions.

Characterization of a 5′-aldehyde terminus resulting from the oxidative attack at C5′ of a 2-deoxyribose on DNA

The 5′-aldehyde terminus is a DNA oxidative damage resulting from attack at C5′ of 2-deoxyriboses by some potent natural or chemical DNA cleavers. To offer a fast and specific method for characterization of this type of damage, we used on-line electrospray ionization mass spectrometry (ESI-MS) detection during liquid chromatography analyses. The intrinsic reactivity of 5′-aldehyde terminus with nucleophiles (formation of hydrate with water, of a Tris adduct with Tris buffer) or through β-elimination reaction resulted in complex LC profiles and MS data. We showed that derivatization of the aldehyde function as an oxime ether gives a stable derivative easy to characterize during on-line ESI-MS analyses. Complete structural characterization of the Tris adduct and the oxime ether derivative were obtained from MS and detailed NMR studies performed on derivatized 5′-aldehyde thymidine models.