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Molecules 2010, 15(8), 5708-5720; doi:10.3390/molecules15085708
Article

Synthesis and Application of a 2-[(4-Fluorophenyl)-sulfonyl]ethoxy Carbonyl(Fsec) Protected Glycosyl Donor in Carbohydrate Chemistry

,  and *
Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden
* Author to whom correspondence should be addressed.
Received: 9 June 2010 / Revised: 10 August 2010 / Accepted: 18 August 2010 / Published: 19 August 2010
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
Download PDF [493 KB, 18 June 2014; original version 18 June 2014]

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 sensitiveprotecting group; O-protection; glycoconjugate synthesis; glycosylation base sensitiveprotecting group; O-protection; glycoconjugate synthesis; glycosylation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Spjut, S.; Qian, W.; Elofsson, M. Synthesis and Application of a 2-[(4-Fluorophenyl)-sulfonyl]ethoxy Carbonyl(Fsec) Protected Glycosyl Donor in Carbohydrate Chemistry. Molecules 2010, 15, 5708-5720.

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