Synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-D-proline relevant to the cell wall O-glycans of green alga Chlamydomonas reinhardtii

The synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-D-proline 1 and 2 with unusual glycan motifs has been achieved efficiently. The assembly of the synthetically challenging 1,2-cis linked arabino- and galactofuranoside frameworks within the targets was realized by the use of a 2-quinolinecarbonyl-assisted 1,2-cis furanosylation approach. (C) 2016 Published by Elsevier Ltd.