Novel approaches to the syntheses of N-substituted S-glycosyl-sulfenamides.
Bis(tetra-O-acetyl-beta-D-glucopyranosyl)disulfide reacts, under silver ion activation, with primary and secondary aliphatic as well as aromatic amines to furnish the title compounds in moderate to good yields. The same derivatives could also be obtained from (tetra-O-acetyl)-beta-D-glucopyranosyl methanethiolsulfonate 1 by nucleophilic substitution with amines. It was shown that the polarization of the S-S-bond in 1 is enhanced by Ag+ so as to allow reaction with sterically hindered amines as well.
Illyés
Tünde-Zita
TZ
Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen Pf. 20, Hungary.
Molnár-Gábor
Dóra
D
Szilágyi
László
L
D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D013416:Sulfamerazine / Q000138:chemical synthesis* / Q000737:chemistry*
D006027:Glycosides; C471392:sulfenamide; D013416:Sulfamerazine