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 is a synthetic nucleoside that is used as an antiviral agent in the treatment of herpes zoster and other viral infections. 5'-O-tert-Butyldimethylsilyl-D3-thymidine is a novel monophosphate, which can be activated to a diphosphate by either kinases or phosphoramidites. It has been shown to be effective against herpes virus and other DNA viruses that infect cells from various species.

Uses

5'-O-(tert-Butyldimethylsilyl)thymidine is used as pharmaceutical intermediate.

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

• 50-89-5 thymidine 
• 3416-05-5 3'-Deoxythymidine 
• 401813-08-9 3-O-(4,4'-dimethoxytrityl)-1,2-dideoxy-D-ribose 
• 401813-07-8 {(2R,3S)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxy}-tert-butyl-dimethyl-silane 
• 65-71-4 thymin 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 1259874-63-9 C₂₉H₃₁N₂O₁₂P 
• 1259875-21-2 5'-O-tert-butyldimethylsilyl-3'-azido-3'-deoxy-3-benzoylthymidine 
• 1259875-23-4 3'-azido-3'-deoxy-3-benzoylthymidine 
• 1259875-25-6 C₂₂H₂₆N₅O₁₀P 
• 1260213-84-0 cis-((5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl) (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl phenyl phosphate 
• 1260213-83-9 cis-((4-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-dioxolan-2-yl)methyl) (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl phenyl phosphate 

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.