The first example of C-glucopyranosides

Autor: Mario Anastasia, Alberto Fiecchi, Pierangela Ciuffreda, Antonio Scala, P. Allevi
Rok vydání: 1990
Předmět:
Zdroj: Chemistry and Physics of Lipids. 53:219-230
ISSN: 0009-3084
DOI: 10.1016/0009-3084(90)90048-v
Popis: Treatment of 2,3,4,6- tetra -O- benzyl - d - glucopyranose trifluoroacetate with the appropriate steroid afforded the starting C- glycopyranosides for the synthesis of 1-(5α-cholestan-3β-yl)-2-β- d -glucopyranosyl-1-ethanone (IV), 1-(5α-cholestan-3β-yl)-2-β- d -glucopyranosylethane (VI), 3β-hydroxy-16β-(β- d -glucopyranosyl)-5α-androstan-17-one (X), 3β-hydroxy-21-β- d -glucopyranosyl-5-pregnen-20-one (XIV), 2-β- d -glucopyranosyl-1,3,5-estratriene-3,17β-diol (XVI), 2-β- d -glucopyranosyl-3-hydroxy-1,3,5-estratrien-17-on (XVIII) These compound represent the first examples of steroidic C-glucosides, a new class of compounds useful as possible enzyme inhibitiors. Unambiguous determination of the structure of all compounds was obtained by means of the 1HNMR spectra at 500 MHz or by chemical transformations.
Databáze: OpenAIRE