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Gold(I)‐Catalyzed Glycosylation with Glycosyl \ \ ortho\ \ ‐Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin by Yao Li; Xiaoyu Yang; Yunpeng Liu; Cunsheng Zhu; You Yang; Biao Yu is a Chemistry article available to read on EtoBox.

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

## 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 amides gives satisfactory yields. Moreover, excellent α‐selective glycosylation with a 2‐deoxy sugar donor and β‐selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective glycosylation of the carboxylic acid and a new one‐pot sequential glycosylation sequence have been implemented.

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

Author

Yao Li; Xiaoyu Yang; Yunpeng Liu; Cunsheng Zhu; You Yang; Biao Yu

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2010

Language

EN

Field

Chemistry (Physical Sciences)