Organic Letters 2003-11-27

Use of olefin cross-metathesis to release azide-containing sugars from solid support.

Takuya Kanemitsu, Peter H Seeberger

Index: Org. Lett. 5 , 4541, (2003)

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Abstract

[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.