1352234-75-3

Upstream product

• 1352234-74-2 C 
• 1005-56-7 phenylcarbonochloridothioate 
• 1352234-69-5 1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose 
• 1352234-70-8 1,2-O-isopropylidene-5-O-benzyl-6-deoxy-3,6-C-divinyl-α-D-gulofuranose 
• 1352234-71-9 C₂₁H₂₆O₇ 
• 1352234-72-0 1-(2-O-acetyl-5-O-benzyl-6-deoxy-3,6-C-divinyl-β-D-gulofuranosyl)thymine 
• 1352234-73-1 C₂₂H₂₄N₂O₇ 
• 1352234-51-5 1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-β-L-arabinopentodialdofuranose 
• 1352234-66-2 1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-6-deoxy-6-C-vinyl-α-D-galactofuranose 
• 1352234-68-4 1,2-O-isopropylidene-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose 
• 532-20-7 L-arabinose 
• 1453105-13-9 1-((2R,3R,3aS,7R,7aS)-7-(benzyloxy)-3,3a-dihydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 103763-12-8 5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose 
• 103763-14-0 (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol 

Downstream Products

• 1352234-76-4 1-((2R,3aS,7R,7aS)-7-(benzyloxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 1352234-77-5 1-((2R,3aS,7R,7aS)-7-(bis(4-methoxyphenyl)(phenyl)methoxy)-3a-hydroxyoctahydrobenzofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 1352234-78-6 (2R,3aS,7R,7aS)-7-(bis(4-methoxyphenyl)(phenyl)methoxy)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-hexahydrobenzofuran-3a(4H)-yl 2-cyanoethyl-N,N-diisopropylphosphoramidite 

Relevant academic research and scientific papers

Synthesis of cis - And trans-α-l-[4.3.0]bicyclo-DNA monomers for antisense technology: Methods for the diastereoselective formation of bicyclic nucleosides

Two α-l-ribo-configured bicyclic nucleic acid modifications, represented by analogues 12 and 13, which are epimeric at C3′ and C5′ have been synthesized using a carbohydrate-based approach to build the bicyclic core structure. An intramolecular l-proline-mediated aldol reaction was employed to generate the cis-configured ring junction of analogue 12 and represents a rare application of this venerable organocatalytic reaction to a carbohydrate system. In the case of analogue 13, where a trans-ring junction was desired, an intermolecular diastereoselective Grignard reaction followed by ring-closing metathesis was used. In order to set the desired stereochemistry at the C5′ positions of both nucleoside targets, a study of diastereoselective Lewis acid mediated allylation reactions on a common bicyclic aldehyde precursor was carried out. Analogue 12 was incorporated in oligonucleotide sequences, and thermal denaturation experiments indicate that it is destabilizing when paired with complementary DNA and RNA. However, this construct shows a significant improvement in nuclease stability relative to a DNA oligonucleotide.

BICYCLIC NUCLEOSIDES AND OLIGOMERIC COMPOUNDS PREPARED THEREFROM

The present invention provides novel 3', 5 '-linked bicyclic nucleosides and oligomeric compounds prepared therefrom. The bicyclic nucleosides provided herein are useful for enhancing one or more properties of the oligomeric compounds they are incorporated into such as nuclease resistance.