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

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Received: 9 June 2010; in revised form: 10 August 2010 / Accepted: 18 August 2010 / Published: 19 August 2010
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(8):5708-5720.

Chicago/Turabian Style

Spjut, Sara; Qian, Weixing; Elofsson, Mikael. 2010. "Synthesis and Application of a 2-[(4-Fluorophenyl)-sulfonyl]ethoxy Carbonyl(Fsec) Protected Glycosyl Donor in Carbohydrate Chemistry." Molecules 15, no. 8: 5708-5720.


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