Synthesis of 1',2'-cis-nucleoside analogues: evidence of stereoelectronic control for SN2 reactions at the anomeric center of furanosides.
We are reporting a highly diastereoselective route to 1',2'-cis-nucleoside analogues in the D-ribo, D-lyxo, D-xylo, and D-arabinoside series. Five-membered ring lactols undergo highly selective N-glycosidation reactions in the presence of dimethylboron bromide with different silylated nucleobases. Stereoelectronic control plays a crucial role for the observed induction, and the products are proposed to be formed through S(N)2 "exploded" transition states. This approach shows great potential considering its simplicity and selectivity for the synthesis of nucleoside analogues, an important class of molecules in medicinal chemistry.
Prévost
Michel
M
Institut de Recherches Cliniques de Montréal (IRCM), Bio-organic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7.
St-Jean
Olivier
O
Guindon
Yvan
Y
D005663:Furans / Q000737:chemistry*; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D005663:Furans; D009705:Nucleosides