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Reactions of sugar nitro-alkenes with 3-aminocrotonic esters

✍ Scribed by Antonio Gomez Sanchez; Manuel Mancera; Francisco Rosado; Juana Bellanato

Book ID
102993169
Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
617 KB
Volume
134
Category
Article
ISSN
0008-6215

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✦ Synopsis

3,4,5,6,7-Penta-O-acetyl-l,2-dideoxy-l-nitro-D-gluco-and -D-g&cto-hept-lenitol and 3,4,5,6-tetra-O-acetyl-l,2-dideoxy-l-nitro-D-xylo-hex-l-enitol react with 3-aminocrotonic esters, yielding mixtures of the epimeric Michael adducts. These are thermally stable, and do not cyclize to pyrroles. The structures, configurations, and conformations of these compounds were established on the basis of their spectroscopic and X-ray crystallographic data. The intramolecularly bonded, (2) configuration was deduced for all of them. Mild hydrolysis of adducts with acid yields the corresponding 2-(nitromethylpolyacetoxyalkyl)acetoacetates. *Studies on Sugar Nitro-olefins. Part IV. For Part III, see ref. 1. tThis paper is dedicated to the memory of Prof. F. Garcia Gonz&lez.

πŸ“œ SIMILAR VOLUMES

Reactions of sugar nitro-alkenes with ac
Reactions of sugar nitro-alkenes with acetoacetic esters
✍ Antonio Gomez Sanchez; Manuel Mancera; Francisco Rosado; Manuel Rico πŸ“‚ Article πŸ“… 1984 πŸ› Elsevier Science 🌐 English βš– 464 KB

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