40733-28-6

Basic information

• Product Name: 5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE
• Synonyms: 5'-O-(T-BUTYLDIMETHYLSILYL)THYMIDINE;5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE;5'-O-tert-Butyldimethylsilylthymidine 97%;5-Methyl-5'-O-(tert-butyldimethylsilyl)-2'-deoxyuridine;5'-O-(tert-ButyldiMethylsilyl)thyMidine, 98+%;5'-O-(tert-ButyldiMethylsilyl)thyMidine, 97+%;5'-O-TBDMS-thymidine;1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 40733-28-6
• Molecular Formula: C₁₆H₂₈N₂O₅Si
• Molecular Weight: 356.49
• Mol File: 40733-28-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 198
• Appearance: /
• Density: 1.148 g/cm³
• Refractive Index: 1.507
• PKA: 9.55±0.10(Predicted)
• CAS DataBase Reference: 5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE(40733-28-6)
• EPA Substance Registry System: 5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE(40733-28-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 40733-28-6(Hazardous Substances Data)

Usage

Description

5'-O-(tert-Butyldimethylsilyl)thymidine, also known as 5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE, is a synthetic nucleoside with antiviral properties. It is characterized by its ability to be activated to a diphosphate by either kinases or phosphoramidites, making it a promising candidate for the treatment of various viral infections.

Uses

Used in Pharmaceutical Industry:
5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE is used as a pharmaceutical intermediate for the development of antiviral medications. It is particularly effective against herpes virus and other DNA viruses that infect cells from various species.
Used in Antiviral Applications:
5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE is employed as an antiviral agent in the treatment of herpes zoster and other viral infections. Its activation to a diphosphate allows it to interfere with the viral replication process, thereby inhibiting the spread of the virus within the host cells.
Used in Research and Development:
5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE is also utilized in research and development for the study of viral mechanisms and the development of new antiviral therapies. Its unique properties make it a valuable tool for understanding the interactions between viruses and their hosts, as well as for designing novel treatments to combat viral infections.

InChI:InChI=1/C16H28N2O5Si/c1-10-8-18(15(21)17-14(10)20)13-7-11(19)12(23-13)9-22-24(5,6)16(2,3)4/h8,11-13,19H,7,9H2,1-6H3,(H,17,20,21)/t11-,12-,13+/m1/s1

Upstream product

• 236754-86-2 C₁₀H₁₄N₂O₅SiC₆H₁₄PO₂CH₃ 
• 236754-84-0 (E)-6'-bromo-(5'-deoxy-5'-methylidene)-3'-O-(tert-bytuldiphenylsilyl)thymidine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 

Downstream Products

• 84915-25-3 Bis(o-chlorophenyl) 5'-O-(tert-butyldimethylsilyl)thymidine 3'-phosphate 
• 80817-47-6 Phosphoric acid benzotriazol-1-yl ester (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 
• 80973-42-8 Phosphoric acid benzotriazol-1-yl ester (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2,4-dichloro-phenyl ester 
• 120232-06-6 5'-O-<(1,1-Dimethylethyl)-dimethylsilyl>-3'-O-(phenoxythioxomethyl)thymidine 
• 161678-20-2 Thiocarbonic acid O-[(2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-(4-chloro-phenyl) ester 
• 166758-13-0 5'-O-(tert-butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)thymidine 
• 50-89-5 thymidine 
• 164267-52-1 5'-O-tert-butyldimethylsilyl-3'-O-(4,4'-dimethoxytriphenylmethyl)thymidine 
• 208458-89-3 Phosphorous acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,6-dichloro-phenyl) ester 
• 200335-35-9 Phenyl-carbamic acid (4aR,6S,7R,7aS)-2-[(2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-3-isopropyl-6-methoxy-hexahydro-furo[2,3-e][1,3,2]oxazaphosphinin-7-yl ester 
• 288573-76-2 C₄₀H₅₁N₆O₈PSi 
• 288573-82-0 C₃₉H₄₇N₆O₇PSi 
• 288573-87-5 C₄₁H₅₃N₆O₇PSi 
• 152753-79-2 1-((2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-{[(E)-2-(2-hydroxy-phenyl)-vinyl]-dimethyl-silanyloxy}-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 

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.