189194-84-1

Basic information

• Product Name: 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine
• Synonyms: 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine
• CAS NO: 189194-84-1
• Molecular Weight: 558.631
• Mol File: 189194-84-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine(189194-84-1)
• EPA Substance Registry System: 5'-deoxy-5'-C-(4,4'-dimethoxytrityloxymethyl)thymidine(189194-84-1)

Safety Data

• Hazardous Substances Data: 189194-84-1(Hazardous Substances Data)

Upstream product

• 148522-79-6 C₂₅H₃₈N₂O₆Si 
• 1610517-69-5 C₂₅H₃₆N₂O₅Si 
• 131118-61-1 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 22567-03-9 5'-homothymidine 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 50-89-5 thymidine 
• 142325-11-9 3'-O-t-Butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine 
• 142325-10-8 5′-deoxy-5′-C-methenyl-3′-O-(tert-butyldimethylsilyl)thymidine 
• 189194-83-0 1-[(2R,4S,5R)-5-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 1610517-71-9 C₃₂H₃₃N₅O₆ 
• 130481-61-7 1-(3'-azido-2',3',5'-trideoxy-β-D-allofuranosyl)thymine 

Relevant articles and documents

Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 6′ position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3′ position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension.

Oligodeoxynucleotides with extended 3′- and 5′-homologous internucleotide linkages

3′-Deoxy-3′-C-(hydroxymethyl)thyrnidine (3′-DHMT) and 5′-deoxy-5′-C-(hydroxymethyl)thymidine (5′-DHMT) have been prepared and used for the synthesis of novel oligodeoxynucleotides containing extended internucleotide linkages. Enzymatic stability toward exonuclease III degradation was studied and hybridization properties were tested. The extended 3′-homologous DNA causes complete cessation of exonuclease III degradation while the extended 5′-homologous DNA shows only some decrease in degradation. Duplexes having extended internucleotide linkages show a minor decrease in hybridization stability. Triplex formation with 20-mer duplexes at pH 5.5 and high salt concentration gave almost no decrease in binding affinity when compared with unmodified triplex formation. UV experiments were also performed with oligodeoxynucleotides containing hairpin structures and bulged bases. Extended linkages in the oligodeoxynucleotides gave a small increase in Tm with sequences containing a loop, but no change or only a small decrease was observed when an extra thymidine nucleotide was incorporated in the complementary strand. Acta Chemica Scandinavica 1997.