866219-07-0

Upstream product

• 74936-95-1 (S)-α-<(R)-pyrrolidin-2-yl>benzyl alcohol 
• 885462-68-0 (1R,2S')-α-(pyrrolidin-2-yl)benzyl alcohol 

Downstream Products

• 1089723-15-8 C₅₃H₅₂N₇O₉P 
• 1089723-14-7 C₄₅H₄₈N₇O₆P 
• 1089723-12-5 C₄₂H₄₄N₃O₈P 
• 1089723-13-6 C₄₃H₄₅N₄O₈P 
• 1115247-39-6 C₅₀H₅₉N₆O₈PSi 
• 1115247-40-9 C₅₉H₆₆N₇O₁₀PSi 
• 866219-08-1 C₄₇H₅₆N₃O₉PSi 
• 1115247-38-5 C₄₉H₅₉N₄O₉PSi 
• 1333502-05-8 5′-O-(4,4′-ddimethoxytrityl)-3'-O-[(2R,4S,5R)-5-phenyl-tetrahydro-1H,3H-pyrrolo[1,2-c]-1,3,2-oxazaphospholidin-2-yl]-2′-O-(2-cyanoethoxymethyl)uridine 
• 1333502-06-9 N⁶-acetyl-5′-O-(4,4′-dimethoxytrityl)-3′-O-[(2R,4S,5R)-5-phenyl-tetrahydro-1H,3H-pyrrolo[1,2-c]-1,3,2-oxazaphospholidin-2-yl]-2′-O-(2-cyanoethoxymethyl)adenosine 
• 1333502-07-0 N⁴-acetyl-5′-O-(4,4′-dimethoxytrityl)-3′-O-[(2R,4S,5R)-5-phenyl-tetrahydro-1H,3H-pyrrolo[1,2-c]-1,3,2-oxazaphospholidin-2-yl]-2′-O-(2-cyanoethoxymethyl)cytidine 
• 1477511-05-9 C₄₅H₄₀NO₁₁P 
• 1477511-11-7 C₄₅H₄₀NO₁₁P 

Relevant academic research and scientific papers

Synthesis and cellular activity of stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate oligonucleotides

Stereochemically-pure 2′-O-(2-methoxyethyl)-phosphorothioate (PS-MOE) oligonucleotides were synthesized from new chiral oxazaphospholidine-containing nucleosides. Thermal stability studies showed that the incorporation of Rp-PS linkages increased RNA-binding affinity. In cells, a full Rp-PS-MOE splice-switching oligonucleotide targeting part of the ferrochelatase gene was more potent than its Sp-PS counterpart, but of similar potency to the stereorandom PS-parent sequence.

ENHANCED COUPLING OF STEREODEFINED OXAZAPHOSPHOLIDINE PHOSPHORAMIDITE MONOMERS TO NUCLEOSIDE OR OLIGONUCLEOTIDE

The present invention relates to the field of stereodefined phosphorothioate oligonucleotides and to stereodefining nucleoside monomers and methods of synthesis of stereodefined oligonucleotides. Herein are disclosed solvent compositions which provide enh

LNA CHIRAL PHOSPHOROTHIOATES

The present invention provides stereodefined phosphorothioate LNA oligonucleotide, comprising at least one stereodefined phosphorothioate linkage between a LNA nucleoside and a subsequent (3') nucleoside.

Stereoselective synthesis of P-modified α-glycosyl phosphates by the oxazaphospholidine approach

α-Glycosyl phosphate derivatives are widely known as constituents of biomolecules. To date, several types of non-natural α-glycosyl phosphates including P-modified analogs have been synthesized to investigate their characteristics. Herein a new approach to the stereoselective modification of the intersugar phosphorus atom in α-glycosyl phosphates by use of the oxazaphospholidine method is presented. Via this approach, the dimers of α-glycosyl phosphorothioates and α-glycosyl boranophosphates were obtained efficiently and stereoselectively.

Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units

Nucleoside 3′-O-bicylic oxazaphospholidine derivatives were designed as monomer units for a solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates (PS-ODNs). The trans-isomers of appropriately designed nucleoside 3′-O-bicyclic oxazaphospholidine derivatives were generated exclusively by the reaction between the 3′-OH of the corresponding protected nucleosides and 2-chloro-1,3,2-oxazaphospholidine derivatives. The resultant trans-oxazaphospholidine isomers were configurationally stable, and their diastereopurity was not impaired by epimerization in the presence of an acidic activator during the condensation on a solid support. As a result, the formation of both (Rp)- and (Sp)-phosphorothioate internucleotide linkages by using the oxazaphospholidine monomers and the acidic activator proceeded without any loss of diastereopurity (diastereoselectivity ≥99:1). In addition, ab initio molecular orbital calculations showed that the epimerization of oxazaphospholidine derivatives was most likely to proceed via an edge inversion process that was accelerated by N-protonation. The calculations rationalized not only the relations between the ring structure and the configurational stability of the oxazaphospholidines observed in this study but also the observations reported in the literature that the inversion of tricoordinated organophosphorus compounds were accelerated by acids or nucleophiles.