糖类的从头不对称生物催化和化学催化合成——使用钯催化的立体选择性形式O-糖苷键形成

De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis.

作者信息

Comely Alex C, Eelkema Rienk, Minnaard Adriaan J, Feringa Ben L

机构信息

Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

出版信息

J Am Chem Soc. 2003 Jul 23;125(29):8714-5. doi: 10.1021/ja0347538.

DOI:10.1021/ja0347538

PMID:12862452

Abstract

A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.

摘要

一种用于从头催化不对称合成糖类的新型生物催化与化学催化相结合的方法已经被开发出来。通过酶促拆分获得对映体纯的乙酰氧基吡喃酮已被证明能发生高度立体选择性的钯催化的形式O-糖苷键形成反应。这些方法的组合可应用于糖类的迭代不对称催化合成。