87412-04-2Relevant academic research and scientific papers
SYNTHESIS OF 2'- AND 3'-AZIDO-2',3'-DIDEOXYADENOSINES. PREPARATIVE APPLICATIONS OF THE DEOXYGENATIVE-HYDRIDE SHIFT AND β-ELIMINATION REACTIONS OF O-SULFONYLATED ADENOSINES
Kawana, Nasajiro,Kuzuhara, Hiroyoshi
, p. 87 - 102 (2007/10/02)
2'-Azido-2',3'-dideoxyadenosine (9) has been synthesized from adenosine (1) in 6-8 steps.The key intermediate, N6,O5'-bis(4,4'-dimethoxytrityl)-9-(3-deoxy-β-D-threo-pentofuranosyl)adenine (6a), was prepared in a one-flask manner by t
Synthesis and conformation of 1-(3'-C-methyl-2'-deoxy-β-D-xylofuranosyl)uracil and 9-(3'-C'-methyl-2'-deoxy-β-D-xylofuranosyl)adenine; two novel sugar-methylated nucleoside analogues
Koole, L. H.,Moody, H. M.,Buck, H. M.,Grouiller, A.,Essadiq, H.,et al.
, p. 343 - 346 (2007/10/02)
The preparation and high-resolution 1H NMR conformational analysis of the two novel nucleoside analogues, 1-(3'-C-methyl-2'-deoxy-β-D-xylofuranosyl)uracil (compound 1) and 9-(3'-C-methyl-2'-deoxy-β-D-xylofuranosyl)adenine (compound 2), are described.Compounds 1 and 2show a pronounced preference for the north conformation of the sugar ring.The north conformation corresponds with a sterically favoured equatorial location of the methyl group.The C4'-C5' conformation in 1 and 2 is predominantly γt (trans orientation of O5' and C3').The configuration at C3' in 1 and 2 was corroborated via a one-dimensional NOE experiment.The structure of compound 1 (originally assigned as having the C3'-methyl group on the β-face of the furanosyl moiety) is revised on the basis of these data.
