358625-75-9

Upstream product

• 532-32-1 sodium benzoate 
• 358625-72-6 (1S,3S,4S)-3-(methanesulfonyloxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 
• 55697-37-5 1-(3'-deoxy-β-D-psicofuranosyl)uracil 
• 358625-55-5 1-[4'-azido-3'-deoxy-β-D-psicofuranosyl]uracil 
• 358625-67-9 (1S,3S,4S)-3-(methanesulfonyloxymethyl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 
• 358625-63-5 1-[4'-azido-3'-deoxy-1',6'-di-O-methanesulfonyl-β-D-psicofuranosyl]uracil 
• 358625-48-6 1-[4'-azido-3'-deoxy-1',6'-di-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil 

Downstream Products

• 358625-83-9 (1S,3S,4S)-3-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 
• 358625-79-3 (1S,3S,4S)-3-(hydroxymethyl)-5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 

Relevant academic research and scientific papers

Synthesis of a novel bicyclic nucleoside restricted to an S-type conformation and initial evaluation of its hybridization properties when incorporated into oligodeoxynucleotides

The phosphoramidite (1S,3R,4S)-3-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl) -5-N-(4-monomethoxytrityl)-1-(uracil-1-yl)-5-aza-2-oxabicyclo[2.2.1]heptane 18 of a novel bicyclic nucleoside structure was synthesized from the known 1-(3′-deoxy-β-D-psicofuranosyl)uracil 3. Conformational analysis of its structure verified its expected S-type furanose conformation, and the secondary amino group in the 4′-position allowed for incorporation into oligonucleotides using 5′ → 3′ directed oligonucleotide synthesis as previously described for phosphoramidates. Thermal denaturation studies showed rather large decreases in duplex stabilities of -4.3 and -2.7 °C per modification toward complementary DNA and RNA, respectively.