Stereocontrolled synthesis of beta-D-mannuronic acid esters: synthesis of an alginate trisaccharide.
A facile synthesis route toward beta-linked mannuronic acid oligomers using the corresponding 1-thiomannuronic acid esters in combination with the Ph2SO/Tf2O or NIS/TMSOTf reagent combinations is presented. The presence of the remotely attached carboxylic ester sufficiently influences the electronic environment to allow good to excellent beta-selectivities.
van den Bos
Leendert J
LJ
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Dinkelaar
Jasper
J
Overkleeft
Herman S
HS
van der Marel
Gijsbert A
GA