175672-61-4

Upstream product

• 88287-61-0 1-Amino-2,5-anhydro-1,3-dideoxy-4,6-di-O-p-toluyl-D-ribo-hexitol hydrochloride 
• 132151-65-6 (E)-3-methoxy-2-methylacryloyl isocyanate 
• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 3601-89-6 Hoffer's chlorosugar 

Downstream Products

• 184719-33-3 1-{(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl}-5-methyl-1H-pyrimidine-2,4-dione 
• 184719-29-7 5'-O-(4,4'-dimethoxytriphenylmethyl)thymidine 

Relevant academic research and scientific papers

[(2-deoxy-α- and β-D-erythro-pentofuranosyl)thymin-1-yl] methane derivatives as potential conformational probes for altDNA oligonucleotides

The previously unknown deoxyribonucleoside analogues 2a,b have been efficiently synthesized from commercial 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose. The conversion of these nucleosides to the phosphoramidite derivatives 13a,b and 14a,b for subsequent incorporation into oligodeoxyribonucleotide analogues is also described.

Synthesis of (2-deoxy-α- and -β-D-erythro-pentofuranosyl)(thymin-1-yl)alkanes and their incorporation into oligodeoxyribonucleotides. Effect of nucleobase-sugar linker flexibility on the formation of DNA-DNA and DNA-RNA hybrids

On the basis of modeling studies, the (2-deoxy-α- and β-D-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-D-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-0-p-toluoyl-D-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b-30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3′ → 5′)- or a (3′ → 3′)-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3′ → 3′)-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its complementary unmodified RNA sequence (ΔTm = 6°C) than for the corresponding DNA sequence (ΔTm = 10°C). This hybrid was, however, thermodynamically less stable than the duplex having unmodified α-2′-deoxythymidine similarly incorporated into 31 (ΔΔTm = 3°C).