244631-67-2

Upstream product

• 50-89-5 thymidine 
• 244631-64-9 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine 
• 244631-63-8 3',5'-di-O-tert-butyldimethylsilyl-5-methoxyacetyloxymethyl-N³-pivaloyloxymethyl-2'-deoxyuridine 
• 244631-61-6 5-acetyloxymethyl-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxyuridine 
• 244631-60-5 5-bromo-3',5'-di-O-tert-butyldimethylsilyl-N³-pivaloyloxymethyl-2'-deoxythymidine 
• 196200-56-3 3',5'-di-O-tert-butyldimethylsilyl N³-pivaloyloxymethyl-2'-deoxythymidine 
• 244631-62-7 3',5'-di-O-tert-butyldimethylsilyl-5-hydroxymethyl-N³-pivaloyloxymethyl-2'-deoxyuridine 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 244631-66-1 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-2'-deoxy-N³-pivaloyloxymethyluridine 

Downstream Products

• 244631-58-1 5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxymethyl-5'-O-(4,4'-dimethoxytrityl)-N³-pivaloyloxymethyl-2'-deoxyuridine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 

Relevant academic research and scientific papers

Synthesis of oligodeoxynucleotides containing 5-(β-D- glucopyranosyloxymethyl)-2'-deoxyuridine, a modified nucleoside in the DNA of Trypanosoma brucei

The synthesis of the recently discovered modified DNA base 5-(β-D- glucopyranosyloxymethyl)-2'-deoxyuridine (β-dJ, 1) is described. TMSOTf mediated β-glucosylation of 5-hydroxymethyl-2'-deoxyuridine (5-HMdU) derivative 10 (obtained in 20% from 2'-deoxyuridine) with trichloroacetimidate 12 gave dimer 13 in 47% yield. On the other hand, condensation of 12 with N3-POM-protected derivative 20, readily available from thymidine in 48%, afforded the fully protected nucleoside 22 in 96% yield. The latter compound was converted into phosphoramidite 3 which was applied in the automated solid phase synthesis of several biological interesting β-dJ containing DNA fragments.