Use of olefin cross-metathesis to release azide-containing sugars from solid support.
[reaction: see text] The octenediol linker used during automated oligosaccharide assembly is cleaved by olefin cross-metathesis. Until now, this linker could not be applied to sugars containing azides. A detailed study of the cleavage reaction served as basis for the development of a new protocol using the [(H(2)Imes)(3-Br-py)(2)(Cl)(2)Ru=CHPh] catalyst and 1-pentene. Efficient release of azide-protected carbohydrates from solid support can be readily achieved.
Kanemitsu
Takuya
T
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Seeberger
Peter H
PH
D000475:Alkenes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000096:biosynthesis / Q000737:chemistry*; D015394:Molecular Structure
D000475:Alkenes; D001386:Azides; D002241:Carbohydrates; C410454:1-pentene