Synthesis and application of a 2-[(4-fluorophenyl)sulfonyl]ethoxy carbonyl (Fsec) protected glycosyl donor in carbohydrate chemistry
2010 (English)In: Molecules, ISSN 1420-3049, Vol. 15, no 8, 5708-5720 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2010. Vol. 15, no 8, 5708-5720 p.
base sensitiveprotecting group, O-protection, glycoconjugate synthesis, glycosylation
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:umu:diva-33838DOI: 10.3390/molecules15085708ISI: 000281481100039OAI: oai:DiVA.org:umu-33838DiVA: diva2:318248