PubMed · 13357340
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S PESONEN, E RAMSTAD. 1956. Studies on gentiopicrin.. https://doi.org/10.1002/jps.3030450805
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Benzyl, benzoyl, and acetyl protected 1-OH and 1-SH glycoses in the glucose, glucosamine, galactose, mannose, and lactose series react with nitrobenzenes activated by one or two electron withdrawing substituents like nitro and cyano to afford the corresponding aryl glycosides in 50-100% yield. The S(N)Ar displacement of nitrite by 1-OH glycoses is reversible and gives predominantly the alpha-glycosides, whereas 1-SH glycoses do not anomerize and afford the beta-glycosides. Thus, the prepared dicyanophenyl gycosides are useful building blocks for the preparation of phthalocyanine-glycoconjugates via template synthesis.
Unsaturated fatty alkyl xylosides and the corresponding 1-O-acyl esters were prepared. Critical micellar concentrations, surface tension areas per molecule and foaming value of some of these new amphiphilic compounds have been determined.
A new phenolic glycoside, 2'-hydroxy-4',6'-di-O-beta-D-glucopyranosyl-butyrrophenone (1), was isolated from the aerial parts of Solidago canadensis. The structure was elucidated on the basis of spectroscopic methods.