Improved Method for the Synthesis of 2-Alkylamino-2-deoxy-d -glucopyranose and 1,2-Dialkylamino-1,2-dideoxy-d -(N)- β-glucoside
| Autor: | Peter S. Piispanen, Torbjörn Norin |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
Glycosylamine
Molecular Structure Organic Chemistry Chemistry Organic Water Fructose Hydrogen-Ion Concentration Chemical synthesis Medicinal chemistry Catalysis Surface-Active Agents Hydrolysis chemistry.chemical_compound Glucose Glucosides chemistry Zinc Compounds Diamine Amadori rearrangement Organic chemistry Amine gas treating Amines Derivative (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 68:628-630 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo026461f |
| Popis: | An improved method for the synthesis of two types of carbohydrate-based, pH-sensitive surfactants has been developed. The surfactants are formed in almost quantitative yields from d-fructose and suitable alkylamines, when using a zinc halide salt as catalyst. The reaction proceeds via an initial Amadori reaction, and the 1,2-dialkylamino-1,2-dideoxy-d-(N)-beta-glucoside precipitates out of the reaction. The product can easily be hydrolyzed to the more water-soluble, surface-active, and pH-sensitive monoalkyl derivative 2-alkylamino-2-deoxy-d-glucopyranose. Products from several amines can be prepared. |
| Databáze: | OpenAIRE |
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