Novel approaches to the syntheses of N-substituted S-glycosyl-sulfenamides

Graphic Bis(tetra- O-acetyl-β- 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)-β- d-glucopyran...

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Bibliographic Details
Published in:Carbohydrate research 2004-06, Vol.339 (8), p.1561-1564
Main Authors: Illyés, Tünde-Zita, Molnár-Gábor, Dóra, Szilágyi, László
Format: Article
Language:English
Subjects:
Disulfide
Glycosides - chemistry
Methanethiolsulfonate
Molecular Structure
Silver ion activation
Sulfamerazine - chemical synthesis
Sulfamerazine - chemistry
Sulfenamide
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Summary:Graphic Bis(tetra- O-acetyl-β- 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)-β- 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.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2004.03.023