28309-53-7

Upstream product

• 25383-78-2 (3aS)-2t-acetoxymethyl-3c-hydroxy-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 108-24-7 acetic anhydride 
• 141-78-6 ethyl acetate 
• 58-96-8 uridine 
• 3736-77-4 2,2'-Anhydrouridine 
• 116597-18-3 1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)uracil 
• 102935-21-7 O^5'-acetyl-O^2'-(toluene-4-sulfonyl)-uridine 
• 109368-38-9 O^5'-acetyl-2'-iodo-2'-deoxy-uridine 
• 22329-20-0 (6R,7R,8S,9R)-7,8-dihydroxy-7,8,9,10-tetrahydro-2H,6H-6,9-epoxypyrimido[2,1-b][1,3]oxazocin-2-one 
• 115259-97-7 3'-O-acetyl-2,5'-anhydrouridine 
• 115259-98-8 3'-O-acetyl-2,5'-anhydro-2'-O-triflyluridine 
• 68-12-2 N,N-dimethyl-formamide 
• 75149-70-1 C₁₁H₁₂N₂O₆*H⁽¹⁺⁾ 
• 127-09-3 sodium acetate 

Downstream Products

• 3736-77-4 2,2'-Anhydrouridine 
• 3083-77-0 araU 

Relevant academic research and scientific papers

2,2′-Anhydro-1-(3′,5′-di-O-acetyl-β-d- arabinofuranosyl)uracil, a cyclouridine nucleoside with a C4′- endo furanosyl conformation

2,2′-Anhydro-1-(3′,5′-di-O-acetyl-β-d- arabinofuranosyl)uracil, C13H14N2O7, was obtained by refluxing 2′,3′-O-(methoxymethylene)uridine in acetic anhydride. The structure exhibits a nearly perfect C4′- endo (4 E) conformation. The best four-atom plane of the five-membered furanose ring is O - C - C - C, involving the C atoms of the fused five-membered oxazolidine ring, and the torsion angle is only -0.4 (2)°. The oxazolidine ring is essentially coplanar with the six-membered uracil ring [r.m.s. deviation = 0.012 (5) A and dihedral angle = -3.2 (3)°]. The conformation at the exocyclic C - C bond is gauche-trans which is stabilized by various C - H...π and C - O...π interactions. Copyright

New telluride-mediated elimination for novel synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides

(Chemical Equation Presented) Several 2′,3′-dideoxynucleosides (ddNs) and 2′,3′-didehydro-2′,3′-dideoxynucleosides (d4Ns) are FDA-approved anti-HIV drugs. Via conveniently synthesized 2,2′-anhydronucleosides, we have developed a novel synthesis of d4Ns by discovering and applying a new telluride-mediated elimination reaction. Our experiment results show that after substitution of 2,2′-anhydronucleosides with a telluride monoanion, a telluride intermediate is formed, and its elimination leads to formation of the olefin products (d4Ns). Our mechanistic study indicates that this telluride-assisted reaction consists of two steps: substitution (or addition) and elimination. By using dimethyl ditelluride (0.1 equiv) as the reagent, d4Ns can be synthesized with yields up to 90% via this telluride-mediated elimination. Our novel strategy has great potential to simplify synthesis of these drugs and to further reduce cost of AIDS treatment and will also facilitate development of novel d4N and ddN analogues.