Synthesis and application of a 2-[(4-fluorophenyl)-sulfonyl]ethoxy carbonyl(Fsec) protected glycosyl donor in carbohydrate chemistry.
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.
Spjut
Sara
S
Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden.
Qian
Weixing
W
Elofsson
Mikael
M
D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry; D006031:Glycosylation; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry
C553808:2-((4-fluorophenyl)-sulfonyl)ethoxy carbonyl; D002241:Carbohydrates; D006845:Hydrocarbons, Fluorinated; D010636:Phenols; D005690:Galactose