40615-37-0

Basic information

• Product Name: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-acetate
• CAS NO: 40615-37-0
• Molecular Formula: C33H34N2O8
• Molecular Weight: 586.642
• Mol File: 40615-37-0.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-acetate(40615-37-0)
• EPA Substance Registry System: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-acetate(40615-37-0)

Safety Data

• Hazardous Substances Data: 40615-37-0(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 21090-30-2 3'-O-acetylthymidine 
• 108-24-7 acetic anhydride 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 50-89-5 thymidine 
• 634206-72-7 C₅₉H₆₅N₄O₁₅PSi 

Downstream Products

• 185672-53-1 3'-O-acetyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside 
• 202723-06-6 3'-O-Acetyl-3-(4-methoxybenzyl)-5'-O-(4,4'-dimethoxytrityl)thymidine 
• 203121-58-8 Acetic acid (2R,3S,5R)-2-(hydroxy-{hydroxy-[2-(4-nitro-phenyl)-ethoxy]-phosphorylmethyl}-phosphinoyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 1146622-40-3 C₅₃H₆₆N₄O₁₄Si 
• 1146622-42-5 C₄₇H₅₂N₄O₁₄ 
• 1146622-44-7 C₅₆H₆₉N₆O₁₅P 
• 75145-86-7 3'-O-acetyl-5'-O-tosylthymidine 
• 1370548-56-3 5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-[ (tert-butoxy)carbonyl]-2'-deoxy-3,4-dihydro-3'-O-(2-methoxy-2-oxoethyl)thymidine 
• 1370548-55-2 3'-O-benzyl-5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-[(tert-butoxy)carbonyl]-2'-deoxy-3,4-dihydrothymidine 
• 1370548-54-1 5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-[(tert-butoxy)carbonyl]-2'-deoxy-3,4-dihydrothymidine 
• 1370548-57-4 sodium 5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-[(tert-butoxy)carbonyl]-3'-O-(carboxylatomethyl)-2'-deoxy-3,4-dihydrothymidine 
• 1370548-51-8 3'-O-acetyl-5'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-3-[(tert-butoxy)carbonyl]-2'-deoxy-3,4-dihydrothymidine 
• 1357475-92-3 5'-O-(4,4'-dimethoxytrityl)-3'-O-acetyl-5-(aminomethyl)-2'-deoxyuridine 
• 1345822-30-1 5-(4-hydroxybenzoylaminomethyl)-2'-deoxyuridine triphosphate 

Relevant articles and documents

Alternatives to the 4,4′-dimethoxytrityl (DMTr) protecting group

The 9-phenyl- and the 9-(p-tolyl)-xanthen-9-yl groups 2a and 2b are recommended as alternatives to the 4,4′-dimethoxytrityl group 1 for the protection of the 5′-hydroxy functions in oligonucleotide synthesis.

AN EFFICIENT PROCEDURE FOR THE SOLID PHASE TRITYLATION OF NUCLEOSIDES AND NUCLEOTIDES

The interaction of tetra-n-butylammonium perchlorate with dimethoxytrityl chloride in the presence of 2,4,6-collidine in dichloromethane permitted a rapid and high yield tritylation of nucleosides or nucleotides covalently attached to a solid support.

Synthesis and biological evaluation of triazolyl 13α-estrone-nucleoside bioconjugates

2' -Deoxynucleoside conjugates of 13α-estrone were synthesized by applying the copper-catalyzed alkyne-azide click reaction (CuAAC). For the introduction of the azido group the 5? -position of the nucleosides and a propargyl ether functional group on the 3-hydroxy group of 13α-estrone were chosen. The best yields were realized in our hands when the 3? -hydroxy groups of the nucleosides were protected by acetyl groups and the 5? -hydroxy groups were modified by the tosyl-azide exchange method. The commonly used conditions for click reaction between the protected-5? -azidonucleosides and the steroid alkyne was slightly modified by using 1.5 equivalent of Cu(I) catalyst. All the prepared conjugates were evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cell lines (HeLa, MCF-7 and A2780) and the potential inhibitory activity of the new conjugates on human 17β-hydroxysteroid dehydrogenase 1 (17β-HSD1) was investigated via in vitro radiosubstrate incubation. Some protected conjugates displayed moderate antiproliferative properties against a panel of human adherent cancer cell lines (the protected cytidine conjugate proved to be the most potent with IC50 value of 9 μM). The thymidine conjugate displayed considerable 17β-HSD1 inhibitory activity (IC50 = 19 μM).

A divalent metal-dependent self-cleaving DNAzyme with a tyrosine side chain

The enzymatic incorporation of a phenol-modified 2′-deoxyuridine triphosphate gave rise to a modified DNA library that was subsequently used in an in vitro selection for ribophosphodiester-cleaving DNAzymes in the presence of divalent zinc and magnesium cations. After 11 rounds of selection, cloning and sequencing resulted in 14 distinct sequences, the most active of which was Dz11-17PheO. Dz11-17PheO self-cleaved an embedded ribocytidine with an observed rate constant of 0.20 ± 0.02 min-1 in the presence of 10 mM Mg2+ and 1 mM Zn2+ at room temperature. The activity was inhibited at low concentrations of Hg2+ cations and somewhat higher concentrations of Eu3+ cations.