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Catalytic Iron(III) Chloride Mediated Site‐Selective Protection of Mono‐ and Disaccharides and One Trisaccharide
Author(s) -
Gouasmat Alexandra,
Lemétais Aurélie,
Solles Julien,
Bourdreux Yann,
Beau JeanMarie
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700538
Subject(s) - chemistry , trisaccharide , regioselectivity , tandem , catalysis , combinatorial chemistry , chloride , substrate (aquarium) , oligosaccharide , carbohydrate , reaction conditions , organic chemistry , materials science , oceanography , composite material , geology
Regioselective differentiation of the hydroxy groups of mono‐ and oligosaccharide substrates is necessary to form building blocks that can be used for synthetic transformations. In this paper, we show that iron(III) chloride hexahydrate catalyses the tandem protection of mono‐ and disaccharides to give, in a one‐pot procedure, selectively protected carbohydrate building blocks. This tandem protocol was successfully applied to a trisaccharide. The procedure is easy to carry out; for optimal results, each carbohydrate substrate required a fine tuning of the one‐pot reaction conditions.