原创力文档synthesis and application of a 2-[(4-fluorophenyl)-sulfonyl]ethoxy carbonyl(fsec) protected glycosyl donor in carbohydrate chemistry合成和应用2 -((4-fluorophenyl)磺酰)乙氧基的羰基(fsec)糖基供体在碳水化合物化学保护.pdfVIP
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synthesis and application of a 2-[(4-fluorophenyl)-sulfonyl]ethoxy carbonyl(fsec) protected glycosyl donor in carbohydrate chemistry合成和应用2 -((4-fluorophenyl)磺酰)乙氧基的羰基(fsec)糖基供体在碳水化合物化学保护
Molecules 2010, 15, 5708-5720; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Synthesis and Application of a 2-[(4-Fluorophenyl)-
sulfonyl]ethoxy Carbonyl (Fsec) Protected Glycosyl Donor in
Carbohydrate Chemistry
Sara Spjut, Weixing Qian and Mikael Elofsson *
Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden
* Author to whom correspondence should be addressed; E-Mail: mikael.elofsson@chem.umu.se;
Tel.: +46-90-786-9328.
Received: 9 June 2010; in revised form: 10 August 2010 / Accepted: 18 August 2010 /
Published: 19 August 2010
Abstract: The 2-[(4-fluorophenyl)sulfonyl]ethoxy carbonyl (Fsec) group for protection of
hydroxyl groups has been designed, synthesized, and evaluated. Fsec-Cl was readily
prepared in 91% yield over three steps and subsequently used to protect 4-fluorobenzyl
alcohol in high yield. The Fsec group was cleaved from the resulting model compound
under mild basic conditions e.g., 20% piperidine in DMF and was stable under acidic
conditions, e.g., neat acetic acid. The Fsec group was used to protect the unreactive 4-OH
in a galactose building block that was later used in the synthesis of 6-aminohexyl
galabioside.
Keywords: base sensitive protecting group; O-protection; glycoconjugate synthesis;
glycosylation
1. Introduction
Regioselectivity is often a challenge in glycoconjugate synthesis
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