149774-49-2Relevant academic research and scientific papers
The nitrile oxide-isoxazoline approach to 11-carbon monosaccharides. Conversion of 3-(tetritol-1-yl)-5-(tetrofuranos-4-yl)-2-isoxazolines into 6-deoxyundecoses
McGhie, Karen E.,Paton, R. Michael
, p. 24 - 41 (2007/10/03)
Hydrogenolysis of (5R)-3-(1,2:3,4-di-O-isopropylidene-D-arabino-tetritol-1-yl)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-4,5-dihydroisoxazole afforded the 7-ulose derivative, from which 6-deoxy-D-gluco-D-gluco- and D-manno-D-gluco-undecose derivatives 17 and 18 were prepared by reduction with sodium borohydride or L-Selectride. The configuration of the new stereogenic centre (C-7) in compounds 17 and 18 was established by NMR analysis of their 5,7-O-isopropylidene derivatives. 6-Deoxy-L-manno-D-gluco- and L-gluco-D-gluco-undecose analogues 19 and 20 were prepared similarly from the isomeric 3-(L-arabino-tetritolyl)-4,5-dihydroisoxazole. Removal of the isopropylidene protecting groups from compounds 17 and 20 yielded 3-O-benzyl-6-deoxy-D-gluco- and L-manno-D-gluco-undecopyranoses, which were characterised as their octa-acetate derivatives. The corresponding reaction sequence from 3-(D- and L-arabino-tetritol-1-yl)-5-(2,3-O-isopropylidene-3-O-methyl-α-D-lyxo-tetrofuranos-4-yl)-4,5-dihydroisoxazoles afforded 6-deoxy-D/L-gluco-D-manno and D/L-manno-D-manno-undecose derivatives. Copyright (C) 1999 Elsevier Science Ltd.
Synthesis of eleven-carbon monosaccharides using nitrile oxide/isoxazoline chemistry
McGhie, Karen E.,Paton, R. Michael
, p. 2831 - 2834 (2007/10/02)
A stereocontrolled route to 6-deoxyundecose derivatives has been developed based on cycloaddition of 5-carbon arabinose-derived nitrile oxides to 6-carbon carbohydrate alkenes and reductive hydrolytic cleavage of the resulting isoxazolines.
