104048-51-3Relevant academic research and scientific papers
First stereocontrolled reduction of isoxazoline by hydrogenolysis: A new route to iminosugars via cyclic sulfates
Lemaire, Marielle,Veny, Nicolas,Gefflaut, Thierry,Gallienne, Estelle,Chenevert, Robert,Bolte, Jean
, p. 1359 - 1361 (2002)
The synthesis of four new trihydroxylated piperidines, considered as analogues of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ), was achieved using cyclic sulfate substituted isoxazoline derivatives. The key step is the one-pot reduction of an
SILYL NITRONATES AND NITRILE OXIDES IN ORGANIC SYNTHESIS. A NOVEL ROUTE TO D,L-DEOXYSUGARS. USE OF ALUMINIUM OXIDE AS SOLID PHASE BASE FOR GENERATION OF NITRILE OXIDES FROM HYDROXIMIC ACID CHLORIDES
Torssell, K. B. G.,Hazell, A. C.,Hazell, R. G.
, p. 5569 - 5576 (2007/10/02)
Novel methodology is developed for a three step synthesis of deoxyaldoses and deoxyketoses. 1.Regioselective addition of silyl nitronate or nitrile oxide to a diene. 2.Stereospecific hydroxylation of the double bond. 3.Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline.The syntheses of D.L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described.Basic aluminium oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and olefins.An X-ray diffraction study of compound 13c verifies the stereochemical assignments.
