1241959-16-9Relevant academic research and scientific papers
Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides
Bouton, Jakob,Van Hecke, Kristof,Van Calenbergh, Serge
, p. 4307 - 4316 (2017/06/30)
Azanucleosides, sugar-modified nucleoside analogues containing a 4′ nitrogen atom, have shown a lot of therapeutic potential, e.g. as anti-cancer and antiviral agents. We report the synthesis of a series of 2’-homoazanucleosides, in which the nucleobase is attached to the 2’-position of the pyrrolidine ring via a methylene linker. A suitable orthogonally protected iminosugar was synthesized by ring closing metathesis and dihydroxylation as key steps and further converted to a series of 8 nucleoside analogues through Mitsunobu reaction with suitably protected nucleobases. The 5′ position of the adenine analogue was then further derivatized with thiols to afford 2 additional compounds. The final compounds were evaluated for biological activity.
Synthesis of l-altro-1-deoxynojirimycin, d-allo-1-deoxynojirimycin, and d-galacto-1-deoxynojirimycin from a single chiral cyanohydrin
Van Den Nieuwendijk, Adrianus M. C. H.,Ruben, Mark,Engelsma, Sander E.,Risseeuw, Martijn D. P.,Van Den Berg, Richard J.B.H.N.,Boot, Rolf G.,Aerts, Johannes M.,Brussee, Johannes,Van Der Marel, Gijs A.,Overkleeft, Herman S.
supporting information; experimental part, p. 3957 - 3959 (2010/11/19)
The chemoenzymatic synthesis of three 1-deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction-transimination-sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.
