142822-32-0Relevant academic research and scientific papers
New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues
Al Mourabit,Beckmann,Poupat,Ahond,Potier
, p. 3455 - 3464 (2007/10/03)
New C2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(β-D-ribofuranosyl)imidazolium 7 and 1-(β-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared. For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity, against HIV and cytotoxicity.
Synthese Stereoselective de la Girolline
Ahond, Alain,Mourabit, Ali Al,Bedoya-Zurita, Manuel,Heng, Richard,Braga, Raquel Marques,et al.
, p. 4327 - 4346 (2007/10/02)
Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereomeric derivatives have been separated.The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose : this ose is condensed with formamidine acetate to obtain a 4(5)--imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.Key Words: girolline synthesis; 2-aminoimidazole; D(-)-arabinose; 4(5)imidazole; rhodium reduction.
