n‑Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies

We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg­(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to...

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Veröffentlicht in:Organic letters 2019-10, Vol.21 (20), p.8270-8274
Hauptverfasser: Zu, Yujia, Cai, Chenglin, Sheng, Jingyuan, Cheng, Lili, Feng, Yingle, Zhang, Shengyong, Zhang, Qi, Chai, Yonghai
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container_end_page 8274
container_issue 20
container_start_page 8270
container_title Organic letters
container_volume 21
creator Zu, Yujia
Cai, Chenglin
Sheng, Jingyuan
Cheng, Lili
Feng, Yingle
Zhang, Shengyong
Zhang, Qi
Chai, Yonghai
description We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg­(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg­(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentiotetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.
doi_str_mv 10.1021/acs.orglett.9b03038
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title n‑Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies
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