G. A. Tolstikov, A. G. Mustafin, G. Kh. Yghibaeva, R. R. Gataullin, L. V. Spirikhin, V. S. Sultanova, I. B. Abdrakhmanov, “<i>N</i>- and <i>C</i>-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester”, Mendeleev Commun., 1993, Volume 3, Issue 5,Page 194

This article is cited in 3 papers

N- and C-Glycosylation of 6,7-Difluoro-1,4-dihydro-4-oxo-3-quinoline Carboxylic Acid Ethyl Ester

G. A. Tolstikov^a, A. G. Mustafin^b, G. Kh. Yghibaeva^b, R. R. Gataullin^b, L. V. Spirikhin^b, V. S. Sultanova^b, I. B. Abdrakhmanov^b

^a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^b Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: 1,2,3,4,6-Penta-O-acetyl-α-D-glucopyranose reacts with a silylated ethyl ester of 6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 1 with C-glycosylation to subsequently afford the ethyl ester of 8-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)- 6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 4; on the contrary, condensation of 1,2-di-O-acetyl-3,5-di-O-benzoyl- D-xylofuranose with the heterocycle 1 results in an N-glycosylation product 2.

Language: English

DOI: 10.1070/MC1993v003n05ABEH000284