Screening of Activation Tools to Design Sulfated Saccharides

O ‐Sulfonation of saccharides using thermal, microwave and flow chemistry activation modes is described. To this end, we studied the exhaustive monosulfation at position 4 and disulfation at positions 4,6 of several monosaccharides bearing a large variety of protecting groups. Additionally the regioselective 6‐ O sulfonation of 4,6‐diol was explored. It is demonstrated that microwave and flow chemistry activation provide significant benefits compared to classical thermal O ‐sulfonation, drastically reducing the reaction time and/or the amount of sulfating reagent. To prove the versatility of the strategy, one example of 6‐ O ‐sulfonation of a disaccharide is also reported.