305819-88-9

Upstream product

• 50-89-5 thymidine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 101527-40-6 5'-O-tert-butyldiphenylsilylthymidine 

Downstream Products

• 305819-95-8 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-phosphono-β-D-threo-pentofuranosyl)thymine 
• 150585-25-4 C₂₇H₃₃⁽²⁾HN₂O₇SSi 
• 101527-40-6 5'-O-tert-butyldiphenylsilylthymidine 
• 166955-29-9 1-[5-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]thymine 
• 305820-01-3 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-C-diethylphosphono-3-O-trimethylsilyl-β-D-threo-pentofuranosyl)thymine 
• 398456-09-2 C₅₄H₆₅N₅O₁₀Si₂ 
• 398456-08-1 C₅₂H₆₃N₅O₉Si₂ 
• 398456-07-0 C₅₂H₆₁N₅O₉Si₂ 
• 398456-05-8 5'-O-tert-butyldiphenylsilyl-3'-O-phthalimido-thymidine 
• 398456-06-9 3'-O-amino-5'-O-tert-butyldiphenylsilyl-thymidine 
• 150585-24-3 (5'-O-tert-butyldiphenylsilyl-2'-deoxy-3'-deutero-β-D-xylofuranosyl)thymine 

Relevant academic research and scientific papers

Phosphorus pentachloride promoted gem-dichlorination of 2′- and 3′-deoxynucleosides

Halogen substitution at various positions of canonical nucleosides has generated a number of bioactive structural variants. Herein, the synthesis of two unique series of sugar modified nucleosides bearing a gem-dichloro group is presented. The synthetic plan entails the controlled addition of phosphorus pentachloride to suitably protected 2′- or 3′-ketodeoxynucleoside intermediates as the key step, facilitating the rapid construction of such functionalized molecules. Under the same reaction conditions, the highest chemoselectivity was observed for the formation of 2′,2′-dichloro-2′,3′-dideoxynucleosides, while a competing 2′,3′-elimination process occurred in the case of the 3′,3′-dichloro counterparts.

Efficient synthesis of 2'-deoxynucleoside 3'-C-phosphonates: Reactivity of geminal hydroxyphosphonate moiety

In this report we present a novel, simple way for the synthesis of 3'-C-phosphonate derivatives of all four basic 2'-deoxynucleosides in both fully protected and deprotected forms. The reactivity of the geminal hydroxy phosphonate moiety located at the 3'

Syntheses and conformational studies on AZT and its deuterated analogues

The NMR spectrum of 3′-azido-3′-deoxythymidine (AZT) in aqueous solution provides sum of some of the proton-proton coupling constants. This limitation precludes the determination of the pseudorotational parameters of the sugar ring. Selective deuteration alleviates this problem. The synthesis of 2′-deutero and 3′-deutero- AZT have been described for the first time starting from D-xylose and β-thymidine respectively. NMR study of these analogues in aqueous solutions shows that almost equal amount of C-2′-endo and C-3′-endo species exist in equilibrium.