Premium
Screening of Activation Tools to Design Sulfated Saccharides
Author(s) -
Ledru Hélène,
D'Attoma Joseph,
Bostyn Stéphane,
Routier Sylvain,
Buron Frédéric,
LopinBon Chrystel
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701853
Subject(s) - reagent , sulfation , monosaccharide , chemistry , disaccharide , microwave , diol , combinatorial chemistry , regioselectivity , organic chemistry , catalysis , biochemistry , computer science , telecommunications
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.