90865-76-2

Upstream product

• 21090-30-2 3'-O-acetylthymidine 
• 160971-72-2 (Sp)-5'-O-DMT-thymidine-3'-O-(Se-methyl methanephosphonoselenolate) 
• 129395-84-2 (R)-Methyl-phosphonothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester S-methyl ester 
• 266361-02-8 (S_P)-5'-O-DMT-thymidine 3'-O-(S-phenyl methanephosphonothioate) 
• 266361-06-2 (R_P)-5'-O-DMT-thymidine 3'-O-(S-phenyl methanephosphonothioate) 
• 129395-81-9 (S)-Methyl-phosphonothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester S-methyl ester 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 88121-80-6 C₃₂H₃₄ClN₂O₈P 

Downstream Products

• 264885-99-6 C₅₅H₆₄N₆O₂₀P₂ 

Relevant academic research and scientific papers

One-pot synthesis of nucleoside 3'-O-(S-phenyl methanephosphonothioates)

The one-pot reaction of nucleosides with McP(O)Cl2 and thiophenol, providing nucleoside 3'-O-(S-phenyl methanephosphonothioate), potential monomers for the synthesis of oligonucleoside methanephosphonate, is described. (C) 2000 Elsevier Science Ltd.

Oligomeric building block approach to the synthesis of diastereomerically pure pentathymidine 3′,5′-methanephosphonates

formula presented A method for a large-scale synthesis of stereodefined oligo(nucleoside 3′,5′-methanephosphonates) has been developed, based on transient 3′-O protection, which allows for the conversion of the protecting chirally defined methanephosphonanilidate group, located at the 3′ end of a stereoregular oligomer, into diastereomerically pure oligomeric building blocks for stereospecific coupling with the 5′-OH group of another oligonucleotide.

Stereochemistry of the DBU/LiCl-Assisted Nucleophilic Substitution at Phosphorus in Nucleoside-3′-O-(Se-methyl Methanephosphonoselenolate)s

The crystal and molecular structure of diastereomerically pure N4-benzoyl-2′-deoxycytidine 3′-O-(Se-methyl methanephosphonoselenolate (FAST-eluted) (4, R = H, B = CBz) and 5′-O-pixylthymidine 3′-O-(S-methyl methanephosphonothiolate (FAST-eluted) (5) have been elucidated by X-ray crystallography. The absolute configuration at the phosphorus atom in both compounds is Sp. Each FAST-4′ (R = DMT, B = CBz) and FAST-5 (R = Px, B = Thy) in the process of DBU/LiCl-assisted condensation with 3′-O-acetyl-A4-benzoylcytidine and 3′-O-acetylthymidine gave after deprotection (Sp)-dicytidine-(3′,5′)-methanephosphonate and (SP)- dithymidine-(3′,5′)-methanephosphonate, respectively. Unambiguous assignment of the absolute configuration at the phosphorus in 4 (R = H, B = CBz) and 5 (R = Px, B = Thy) allows for stereochemical correlation and the conclusion that DBU/LiCl-assisted nucleophilic substitution at phosphorus occurs with net inversion of configuration, in contrast to our earlier erroneous deduction.5 Moreover, the knowledge of the absolute configuration at the phosphorus atom in both 4 (R = H, B = CBz) and 5 (R = Px, B = Thy) allows for assignment of the absolute configuration at phosphorus in precursors of 4′ and 5, such as 5′-O-DMT-nucleoside 3′-O- methanephosphonothioanilidates (6), methanephosphonoanilidates (8), and methanephosphonoselenoanilidates (9).

New stereospecific method of synthesis of [Sp]-and [Rp]-dinucleoside-(3',5') methanephosphonates

Using a stereoretentive reaction between diastereomerically pure 5'-O-DMT-(N-protected) nucleoside 3'-O-(Se-methyl methanephosphonoselenolate)s and 3'-O-acetyl-(N-protected) nucleosides, diastereomerically pure dinucleoside-(3',5') methanephosphonates as