• Abstract
• Full-Text PDF [493 KB]

• Article Statistics
• PubMed/Medline
• Google Scholar
• Order Reprints

• Cite this article
• Export to BibTeX
• Export to EndNote

• [+] on DOAJ
• Spjut, S
• Qian, W
• Elofsson, M
• [+] on Google Scholar
• Spjut, S
• Qian, W
• Elofsson, M
• [+] on PubMed
• Spjut, S
• Qian, W
• Elofsson, M

•  CiteULike
•  Facebook
•  Mendeley
•  Twitter

This article is

• freely available
• re-usable

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

Sara Spjut, Weixing Qian and Mikael Elofsson*

Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden

* Author to whom correspondence should be addressed.

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)

Download PDF Full-Text [493 KB, Updated Version, uploaded 25 August 2010 10:52 CEST]

The original version is still available [213 KB, uploaded 19 August 2010 12:12 CEST]

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

Article Statistics

Cite This Article