121611-66-3Relevant academic research and scientific papers
Synthesis and antiviral evaluation of α-l-2′- deoxythreofuranosyl nucleosides
Toti, Kiran S.,Derudas, Marco,McGuigan, Christopher,Balzarini, Jan,Van Calenbergh, Serge
experimental part, p. 3704 - 3713 (2011/11/07)
The synthesis of a series of α-l-2′-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-l-threose, involving a Vorbru?ggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase.
NOVEL SYNTHETIC EQUIVALENTS OF DIFFERENTIALLY PROTECTED TARTARIC ALDEHYDES. A SIMPLE ROUTE TO USEFUL C-4 CHIRAL SYNTHONS.
Dhavale, Dilip D.,Tagliavini, Emilio,Trombini, Claudio,Umani-Ronchi, Achille
, p. 6163 - 6166 (2007/10/02)
The synthesis of 4-acetoxy-3-O-benzyl-1,2-O-isopropylidene aldotetroses from D-glucose is reported.These synthetic equivalents of tartaric aldehydes are chemoselectively reduced at the acetoxylated center leading to a series of useful differentially protected C-4 chiral synthons.
