127219-58-3Relevant articles and documents
N-GLUCOSYLATION OF AMINOINDOLINES AND THE BISGLUCOSIDES OF 5-AMINOINDOLE
Salekh, M. A.,Krasavina, L. S.,Vigdorchik, M. M.,Turchin, K. F.,Sapukova, A. A.,et al.
, p. 2348 - 2355 (2007/10/02)
The reaction of 1-acetyl-5- and 1-acetyl-6-aminoindolines with D-glucose gave the N-β-D-glucopyranosides of 1-acetyl-5- and 1-acetyl-6-aminoindolines, the β-configurations of which were preserved during conversion into the O-acetylated derivatives.The reaction of D-glucose with 5-aminoindoline followed by O-acetylation gave the O-acetylated bis-N1,N5-glucopyranoside of 5-aminoindoline as a mixture of the 1β,5β and 1β,5α anomers.Dehydrogenation followed by O-deacetylation led to the bis-N1,N5-glucopyranoside of 5-aminoindole also as a mixture of the 1β,5β and 1β,5α anomers.During the N-acetylation of the O-acetylated bis-N1,N5-glucoside of 5-aminoindoline the corresponding 5-acetamide derivative was obtained in the form of the individual 1β,5β anomer, which was converted after dehydrogenation and O-deacetylation into the individual 1β,5β anomer of the bis-N1,N5-glucopyranoside of 5-acetamidoindole.
