1200119-13-6Relevant articles and documents
Stereoselective construction of 1β-azido- And 1β-cyano-2-deoxyribose derivatives
Fujioka, Hiromichi,Moriya, Takahiro,Okamoto, Kazuhisa,Minamitsuji, Yutaka,Ueyama, Yoshifumi,Matsumoto, Nao,Murai, Kenichi
, p. 1142 - 1157 (2015)
A new method has been developed for the β-selective introduction of azido and cyano groups at the anomeric position of 2-deoxyribose derivatives. This method proceeds via the formation of a collidinium salt intermediate and allows for the stereoselective construction of 1β-azido- and 1β-cyano-2-deoxy-D-ribose derivatives. 2-Deoxy-D-ribose compounds bearing an acetoxy or tert-butoxycarbonyloxy group at their anomeric position performed well as starting materials for the formation of the corresponding 1β-azide and 1β-cyanide derivatives, respectively. 1H NMR studies of the salt intermediates revealed that the nucleophilic substitution reaction of the salt intermediates proceeded in a SN2-fashion.