494798-46-8

Upstream product

• 50-89-5 thymidine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 83467-48-5 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 494798-45-7 3'-O-tert-butyldiphenylsilyl-5'-C(S)-methyl ethanoate-thymidine 

Downstream Products

• 494798-47-9 5′-C(S)-tosyloxyethyl-3′-O-(tert-butyldiphenylsilyl)thymidine 
• 494798-48-0 C₆₉H₇₆N₅O₁₇PSSi 

Relevant academic research and scientific papers

Thio- and Seleno-Dioxaphosphorinane-Constrained Dinucleotides (D-CNA): Synthesis and Conformational Study

Thio- and seleno-α,β- and α,β,γ-D-CNA (constrained nucleic acid) dinucleotides in which two or three torsion angles of the sugar/phosphate backbone are controlled within a dioxaphosphorinane structure have been prepared. Their structural determination was carried out by means of NMR spectroscopy to show only slight variation on the torsion-angle control in comparison with their oxo analogues. Unexpected selenium migration has been pointed out from selenophosphotriester moiety to phosphoramidite group, but this drawback can be overcome using H-phosphonate chemistry.

Synthesis and structural study of ribo-dioxaphosphorinane-constrained nucleic acid dinucleotides (ribo-α,β-D-CNA)

With increasing interest in the control of the conformations of nucleic acids to define active riboswitch or siRNA, we present herein our efforts towards the stereocontrolled synthesis and conformational analysis of ribodinucleotides in which α and β torsional angles are constrained within a dioxaphosphorinane structure (ribo-α,β-D-CNA). The crystal structure analysis of one α,β-D-CNA TU dimer demonstrates the absolute stereochemistry of the newly created asymmetric centres. NMR and CD analyses allowed complete assignment and the determination of the torsional angles in the α,β-D-CNA UU diastereoisomers. Diastereoisomers of α,β-D-CNA ribodinucleotide building blocks of nucleicacids in which the α and β torsional angles are stereocontrolled by a dioxaphosphorinane ring structure (D-CNA family) have been synthesised. The structural analyses showed that these dinucleotides exhibit a South/North junction associated with either canonical or non-canonical states of the sugar phosphate backbone. Copyright

Diastereoselective synthesis of a conformationally restricted dinucleotide with predefined alpha and beta torsional angles for the construction of alpha,beta-constrained nucleic acids (alpha,beta-CNA).

[reaction: see text] The synthesis of a diastereopure 1,3,2-dioxaphosphorinane linkage in which two, alpha and beta, out of six torsion angles of the natural phosphodiester backbone are constrained with predefined values of ca. +60 degrees (g(+)) and 180