Literature DB >> 30019713

Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors.

Xu Dong1, Li Chen2, Zhitong Zheng3, Xu Ma3, Zaigang Luo3, Liming Zhang3.   

Abstract

A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf2.

Entities:  

Year:  2018        PMID： 30019713      PMCID： PMC6080613          DOI： 10.1039/c8cc02494d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  17 in total

1.  Total synthesis and structural revision of TMG-chitotriomycin, a specific inhibitor of insect and fungal beta-N-acetylglucosaminidases.

Authors:  You Yang; Yao Li; Biao Yu
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

2.  Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation.

Authors:  Yuyong Ma; Gaoyan Lian; Yao Li; Biao Yu
Journal:  Chem Commun (Camb)       Date:  2011-05-31       Impact factor: 6.222

3.  An efficient approach to the synthesis of nucleosides: gold(I)-catalyzed N-glycosylation of pyrimidines and purines with glycosyl ortho-alkynyl benzoates.

Authors:  Qingju Zhang; Jiansong Sun; Yugen Zhu; Fuyi Zhang; Biao Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-15       Impact factor: 15.336

Review 4.  "Active-latent" thioglycosyl donors and acceptors in oligosaccharide syntheses.

Authors:  Tze Chieh Shiao; René Roy
Journal:  Top Curr Chem       Date:  2011

5.  Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates.

Authors:  Yuyong Ma; Zhongzhen Li; Hefang Shi; Jian Zhang; Biao Yu
Journal:  J Org Chem       Date:  2011-11-04       Impact factor: 4.354

6.  Characterization of the isochromen-4-yl-gold(I) intermediate in the gold(I)-catalyzed glycosidation of glycosyl ortho-alkynylbenzoates and enhancement of the catalytic efficiency thereof.

Authors:  Yugen Zhu; Biao Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-20       Impact factor: 15.336

7.  Gold-catalyzed etherification and Friedel-Crafts alkylation using ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent.

Authors:  Naoki Asao; Haruo Aikawa; Sakie Tago; Kazuteru Umetsu
Journal:  Org Lett       Date:  2007-09-20       Impact factor: 6.005

8.  Construction of interglycosidic N-O linkage via direct glycosylation of sugar oximes.

Authors:  Jun Yu; Jiansong Sun; Biao Yu
Journal:  Org Lett       Date:  2012-07-25       Impact factor: 6.005

9.  ortho-(Methyltosylaminoethynyl)benzyl glycosides as new glycosyl donors for latent-active glycosylation.

Authors:  Xiaoping Chen; Dacheng Shen; Qiaoling Wang; You Yang; Biao Yu
Journal:  Chem Commun (Camb)       Date:  2015-09-21       Impact factor: 6.222

10.  Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization.

Authors:  Yu Bai; Xingyu Shen; Yong Li; Mingji Dai
Journal:  J Am Chem Soc       Date:  2016-08-17       Impact factor: 15.419
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