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Carbohydr Res. 2014 Sep 19;396:14-24. doi: 10.1016/j.carres.2014.05.012. Epub 2014 May 26.

Side reactions with 2,2,2-trichloroethoxysulfates during the synthesis of glycans.

Author information

1
Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8552, Japan.
2
Otsuka Chemical Co, Ltd, 463 Kagasuno, Kawauchi-cho, Tokushima 771-0193, Japan.
3
Department of Regional Environment, Faculty of Regional Sciences, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8551, Japan.
4
Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8552, Japan; Department of Regional Environment, Faculty of Regional Sciences, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8551, Japan. Electronic address: jtamura@rs.tottori-u.ac.jp.

Abstract

Protected sulfate groups may be used as an alternative tool to provide sulfate esters at hydroxyl and amino groups, particularly on complex glycans. We examined 2,2,2-trichloroethoxysulfation at the mono-, di-, and trihydroxyl groups of saccharide moieties to show regioselective sulfation. We found some side reactions including inter- and intramolecular nucleophilic reactions with 2,2,2-trichloroethoxysulfates.

KEYWORDS:

2,2,2-Trichloroethoxysulfate; Glycan synthesis; Intramolecular attack; Protected sulfate; Sulfated oligosaccharide

PMID:
25084507
DOI:
10.1016/j.carres.2014.05.012
[Indexed for MEDLINE]
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