173776-23-3

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)acetonitrile is used as a building block in organic synthesis for the production of nucleoside and nucleotide analogs. It serves as a key intermediate in the synthesis of a wide range of biologically active molecules.
Used in Organic Synthesis:
(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)acetonitrile is used as a versatile intermediate for further chemical manipulation. The trityl group acts as a protecting group, preventing unwanted reactions at the anomeric carbon, while the acetonitrile group provides a handle for additional synthetic steps.

Upstream product

• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 124290-99-9 (4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,4-diol 
• 22900-10-3 2-deoxy-D-ribose 
• 76-83-5 trityl chloride 

Downstream Products

• 184719-21-9 (2R,3S,5S)-5-(2-Amino-ethyl)-2-trityloxymethyl-tetrahydro-furan-3-ol 
• 184719-32-2 1-(2-{(2S,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-hydroxymethyl-tetrahydro-furan-2-yl}-ethyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 184719-28-6 1-(2-{(2S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-ethyl)-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

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).

1-(2-Deoxy-α- and β-D-erythro-pentofuranosyl)-2-(thymin-1-yl)ethane Derivatives as Conformational Probes for altDNA Oligonucleotides

The novel deoxyribonucleoside analogues 1a,b have been synthesized in a straightforward manner from 2-deoxy-D-ribose.These modified nucleosides have also been converted to the phosphoramidite derivatives 13a,b and 14a,b for potential incorporation into ol