An efficient and highly diastereoselective synthesis of C-glycosylated 1,3-oxazolidines from N-methyl-d-glucamine
A one-pot procedure for preparing chiral 1,3-oxazolidines derived from N-methyl-d-glucamine and aryl aldehydes is described. It has been carried out by using readily available reagents and operationally simple conditions allowing the preparation of the acyclic C-nucleoside analogs in high yields. The structure of these derivatives has been fully characterized by NMR correlations and single-crystal X-ray diffraction. Some reactions also provide access to the corresponding tetrahydro-1,3-oxazines by an alternative ring closure. Mechanistic considerations account for the observed steric course. Crown Copyright
Martínez, R. Fernando,ávalos, Martín,Babiano, Reyes,Cintas, Pedro,Jiménez, José L.,Light, Mark E.,Palacios, Juan C.,Pérez, Esther M.S.
p. 6377 - 6386
(2008/09/21)
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