Gold (I)??Catalyzed Glycosylation with Glycosyl ortho??Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin

Y Li, X Yang, Y Liu, C Zhu, Y Yang…

Index: Li, Yao; Yang, Xiaoyu; Liu, Yunpeng; Zhu, Cunsheng; Yang, You; Yu, Biao Chemistry - A European Journal, 2010 , vol. 16, # 6 p. 1871 - 1882

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Citation Number: 95

Abstract

Abstract Glycosyl ortho-alkynylbenzoates have emerged as a new generation of donors for glycosidation under the catalysis of gold (I) complexes such as Ph 3 PAuOTf and Ph 3 PAuNTf 2 (Tf= trifluoromethanesulfonate). A wide variety of these donors, including 2-deoxy sugar and sialyl donors, are easily prepared and shelf stable. The glycosidic coupling yields with alcohols are generally excellent; even direct coupling with the poorly nucleophilic ...