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Carbonate Couplers and Functional Cyclic Carbonates from Amino Acids and Glucosamine
Author(s) -
Fricke Nicole,
Keul Helmut,
Möller Martin
Publication year - 2009
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200800497
Subject(s) - chemistry , reactivity (psychology) , reagent , carbonate , glucosamine , polymer chemistry , oxime , coupling reaction , acetone , glycerol , organic chemistry , amino acid , catalysis , medicine , biochemistry , alternative medicine , pathology
On the basis of glycerol carbonate, four coupling reagents 3a‐d were prepared. Their synthesis and characterisation, starting from glycerol carbonate 2 , is described. To evaluate the differences in reactivity these couplers were reacted with valine methyl ester and the results were compared with the already known coupler 3a . Reaction conditions influenced the conversion of the couplers 3a‐d containing phenyl, 4‐nitrophenyl, imidazolyl and acetone oxime leaving groups; highest conversion and fastest reaction rates were obtained with 3b . The coupling reagents 3a and b were used for the synthesis of functional carbonate building blocks from amino acid methyl esters and glucosamine.