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.
THE 1ST EXAMPLE OF STEROIDIC C-GLUCOPYRANOSIDES / P. ALLEVI, M. ANASTASIA, P. CIUFFREDA, A. FIECCHI, A. SCALA. - In: CHEMISTRY AND PHYSICS OF LIPIDS. - ISSN 0009-3084. - 53:2-3(1990), pp. 219-230.
THE 1ST EXAMPLE OF STEROIDIC C-GLUCOPYRANOSIDES
P. ALLEVIPrimo
;M. ANASTASIASecondo
;P. CIUFFREDA;
1990
Abstract
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.
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