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Synthesis of 2-Amino-2-deoxy-1,3-dithioidoglycosides via Organocatalytic Relay glycosylation of 3-O-Acetyl-2-nitrogalactals

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Chinese Journal of Chemistry 2023年第21期41卷 2837-2842页

作者： Yongyong Wan Lei Deng Liming Wang Yuanhong Tu Hui Liu Jian-song Sun Qingju Zhang National Research Centre for Carbohydrate Synthesis Jiangxi Normal University99 Ziyang AvenueNanchangJiangxi330022 China Key Laboratory of Carbohydrate Chemistry and Biotechnology Ministry of EducationSchool of Biotechnologyand Wuxi School of MedicineJiangnan UniversityWuxiJiangsu214122 China

Idose-type glycosides have numerous biological activities and have been widely used as anticoagulant drugs and anti-infection *** have enhanced stability for acid-mediated or enzymatic hydrolysis,and have a wide range of applications in glycobiology and drug ***,we describe an efficient method for site-selective and stereoselective synthesis of potential bioactive 2-amino-2-deoxy-1,3-dithioidoglycosides via organocatalysis sequential C3-Ferrier rearrangement and Michael addition of *** stepwise and one-pot protocols were carried out and work *** unique thio-glycosylation protocol highlighted the various advantages,including(i)mild reaction conditions;(ii)excellent site-selectivity and stereoselectivity,good to excellent yields;(iii)broad substrate scopes;(iv)being atom-economic and environmentally friendly;(v)the reactions can be scaled up.

关键词： Idoglycosides Thioglycosides stereoselective glycosylation 3-O-Acetyl-2-nitrogalactals Organocatalysis Relay glycosylation

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stereoselective Synthesis and Immunological Evaluation of Common O-antigen of P. mirabilis OE and P. vulgaris TG103

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Chinese Journal of Chemistry 2023年第5期41卷 535-543页

作者： Xiaopei Wu Jinsheng Lai Kexin Yang Yunxia Xue Jinxi Liao Liming Wang Jian-song Sun Jing Hu Jian Yin Qingju Zhang National Research Centrefor Carbohydrate Synthesis Jiangxi Normal University99 Ziyang AvenueNanchangJiangxi 330022China Key Laboratory of Carbohydrate Chemistry and Biotechnology Ministryof EducationSchoolof Biotechnology and Wuxi School of MedicineJiangnan UniversityWuxiJiangsu 214122China

Proteus species especially Proteus mirabilis and Proteus vulgaris are zoonotic pathogens which can cause public health *** to their antibiotic-resistance,developing vaccines against these pathogens is urgently ***,we ... 详细信息

关键词： stereoselective glycosylation Proteus mirabilis OE proteus vulgaris TG 103 Common O-antigen Immunological evaluation Syntheticcarbohydrate-based vaccine Total synthesis

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An SN2-Type Strategy toward 1,2-cis-Furanosides

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CCS Chemistry 2022年第12期4卷 3677-3685页

作者： Xu Ma Yongliang Zhang Xijun Zhu Liming Zhang Department of Chemistry and Biochemistry University of CaliforniaSanta BarbaraCA 93106

The stereoselective construction of 1,2-cis furanosidic linkage is synthetically challenging.A strategy that applies to all furanose types remains *** this work,a solution is developed based on gold catalysis and the deployment of the directinggroup-on-leaving-group strategy,where a basic oxazole group in the gold-activated leaving group facilitates the stereoinvertive attack by glycosyl *** addition to exhibiting good to excellent 1,2-cis selectivities,these furanosylation reactions are high-yielding and mostly complete in 30 min to 2 h.A broad range of 1,2-cis-furanosides is *** some are uncommon,the ease of access enabled by this approach presents new opportunities to study their applications in medicine and materials research.

关键词： gold catalysis stereoselective glycosylation 1,2-cis-furanosides furanosylation S_(N)2

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