Use of olefin cross-metathesis to release azide-containing sugars from solid support.
Use of olefin cross-metathesis to release azide-containing sugars from solid support.
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DOI：
10.1021/ol035463z
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发表时间：
2003-10
期刊：
影响因子：
5.2
通讯作者：
T. Kanemitsu;P. Seeberger
中科院分区：
文献类型：
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作者：
T. Kanemitsu;P. Seeberger
[反应：见正文]自动化低聚糖组装过程中使用的辛烯二醇连接体被烯烃交叉复分解裂解。到目前为止，这种连接物还不能应用于含有叠氮化物的糖。对裂解反应的详细研究为开发使用[(H(2)IMES)(3-Br-py)(2)(Cl)(2)Ru=CHPh]催化剂和1-戊烯的新方案奠定了基础。可以容易地从固体载体中有效地释放叠氮保护的碳水化合物。
[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.