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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
Alternative Title金催化邻炔基苯甲酸酯给体的糖苷化反应研究及其在一个环状三萜皂甙合成中的应用
Li Y(李瑶); Yang XY(杨晓瑜); Liu YP(刘运鹏); Zhu CS(祝存生); Yang Y(杨友); Yu B(俞飚)
2010
Source PublicationChem.-Eur. J.
ISSN0947-6539
Volume16Issue:6Pages:1871-1882
AbstractGlycosyl ortho-alkynylbenzoates have emerged as a new generation of donors for glycosidation under the catalysis of gold(I) complexes such as Ph3PAuOTf and Ph3PAuNTf2 (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 alpha-selective glycosylation with a 2-deoxy sugar donor and beta-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.
Subject Area生命有机化学
Department中国科学院上海有机化学研究所; 中国海洋大学; 中国科学技术大学
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Indexed BySCI
Language英语
WOS IDWOS:000275240300021
Citation statistics
Cited Times:137[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/19127
Collection生命有机化学国家重点实验室
Corresponding AuthorYu B(俞飚)
Recommended Citation
GB/T 7714
Li Y,Yang XY,Liu YP,et al. Gold(I)-Catalyzed Glycosylation with Glycosyl ortho-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin[J]. Chem.-Eur. J.,2010,16(6):1871-1882.
APA 李瑶,杨晓瑜,刘运鹏,祝存生,杨友,&俞飚.(2010).Gold(I)-Catalyzed Glycosylation with Glycosyl ortho-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin.Chem.-Eur. J.,16(6),1871-1882.
MLA 李瑶,et al."Gold(I)-Catalyzed Glycosylation with Glycosyl ortho-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin".Chem.-Eur. J. 16.6(2010):1871-1882.
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