Reactions of sugar nitro-alkenes with acetoacetic esters |
| |
| Authors: | Antonio Gomez Sanchez Manuel Mancera Francisco Rosado Manuel Rico |
| |
| Institution: | Department of Organic Chemistry, Faculty of Pharmacy, University of Seville, and Institute of Fat and its Derivatives, C.S.I.C., Seville Spain;Institute of Optics and State of Matter, C.S.I.C., Madrid Spain |
| |
| Abstract: | 3,4,5,6,7-Penta-O-acetyl-1,2-dideoxy-1-nitro-d-gluco-hept-1-enitol reacts with methyl acetoacetate in an unusual Michael reaction, giving the normal adduct (6), and a bicyclic derivative (9) that arises from quasi-dimerization of the former when a high concentration of the base is used. Acetylation of compound 9 gives the hydroxylamine O-acetate (10).From the reactions of 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-d-galacto-hept-1-enitol with ethyl and tert-butyl acetoacetate, the normal adducts (7 and 8) were isolated. The structures of compounds 6 to 10 were established on the basis of their spectral properties (u.v., i.r., mass, and 1H- and 13C-n.m.r.) |
| |
| Keywords: | To whom correspondence should be addressed at Department of Organic Chemistry Faculty of Pharmacy Seville Spain |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
