title: Improved method for the synthesis of 2-alkylamino-2-deoxy-d-glucopyranose and 1,2-dialkylamino-1,2-dideoxy-d-(N)-beta-glucoside.
abstract: 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.
authors.affiliation: Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden.
authors.forename: Peter S
authors.initials: PS
authors.lastname: Piispanen
authors.forename: Torbjörn
authors.initials: T
authors.lastname: Norin
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005632:Fructose / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005960:Glucosides / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D013501:Surface-Active Agents; D014867:Water; D017967:Zinc Compounds / Q000737:chemistry
chemical_list: D000588:Amines; D005960:Glucosides; D013501:Surface-Active Agents; D017967:Zinc Compounds; D014867:Water; D005632:Fructose; D005947:Glucose