Reactions of sugar nitro-alkenes with acetoacetic esters

✍ Scribed by Antonio Gomez Sanchez; Manuel Mancera; Francisco Rosado; Manuel Rico

• Book ID: 102641001
• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 464 KB
• Volume: 134
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(84)85023-5

✦ Synopsis

Penta-O-actyl-l,2-dideoxy-l-nitro-D-gluco-hept-l-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-0-acetyl-1,2-dideoxy-1-nitro-Dgulucto-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 'H-and 13C-n.m.r.) *Studies on Sugar Nitro-olefins, Part V. For Part IV, see ref. 1.