个人简介

课题组网站：https://www.x-mol.com/groups/chaiyonghai

2009年至今就职于陕西师范大学，博导教授。回国后先后主持了“国家重大新药创制计划”课题一项、作为课题副组长参与“国家重大新药创制计划”课题两项，主持国家自然基金上项目两项，陕西省自然基金一项，教育部留学归国人员基金项目一项；主持与企业合作项目两项，开发抗病毒药物分子的设计与合成。

课题组的研究主要分为四个方向：（1）与糖类结构相关的药物分子设计与合成，包括抗肿瘤药物紫杉醇类化合物的糖基化修饰以及基于CMP-KDO合成酶抑制剂的活性分子的设计与合成；（2）快速寡糖分子的合成。本课题组设计合成了一类新型的苄基型氟载体。利用该类氟载体，在反应体系中加入惰性、稳定廉价的氟粒子，课题组可以实现溶液反应条件下快速高效的寡糖及多糖类化合物的合成组装；（3）有机小分子催化的C-C构建。以叔胺或叔膦类化合物为催化剂，活化烯与醛或亚胺类化合物在温和的条件下形成alpha-烯基-beta-羟基类化合物。该反应可以用来高效构建五元杂类环化合物；（4）新型糖苷键化方法学的研究。课题组发展了一种基于金属催化的串联环化反应的新型糖苷键化反应。该类反应的特点在于供体中的端基基团是稳定的保护基，同时在特定的金属催化作用下可以被活化发生糖苷键化反应，是一种具有双重作用的糖基化供体。

研究成果

近期文章及授权专利：

2022

22. Ni(II)-Catalyzed Regio- and Stereoselective O-Alkylation for theConstruction of 1,2-cis-Glycosidic LinkagesYingle Feng*, Tiantian Guo, Han Yang, Guoqiang Liu, Qi Zhang, Shengyong Zhang, andYonghai Chai*.Org. Lett.2022, https://doi.org/10.1021/acs.orglett.2c02419

20. Insights into the Activation of Alkyne-Installed Glycosyl Donors with Dual Acidic Metal Catalysts: Reaction Pathway, Influencing Factors, and Enlightenment for Glycosylation

Chenglin Cai, Xingchun Sun, Yingle Feng, Qi Zhang*, andYonghai Chai*.Org. Lett.2022,https://doi.org/10.1021/acs.orglett.2c02338

19. Catalytic and highly stereoselective β-mannopyranosylation using a 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate as donor

Yingle Feng*, Jie Yang , Chenglin Cai, Taotao Sun, Qi Zhang,YonghaiChai*.Chin. Chem. Lett.2022, 33,4878-4881.

18. Photolabile 2-(2-Nitrophenyl-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides.

Jincai Wang, Yingle Feng*, Taotao Sun, Qi Zhang, andYonghai Chai*.J. Org. Chem.2022, 87, 5,3402–3421

2021

17. Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization.

Aiyun Liu, Tiantian Guo, Shuangshuang Zhang, Han Yang, Qi Zhang*,Yonghai Chai*, and ShengyongZhang*.Org. Lett.2021, 23, 16,6326–6331.

2020

16. Environmentally Benign Access to Isoindolinones: Synthesis, Separation and Resource Recycling.

Weiwei Guo, Qi Zhang, Yang Cao, Kaihua Cai, Shengyong Zhang*, andYonghai Chai*.Green Chem.2020,22, 2873-2878.

15. Fast and Low-Cost Purification Strategy for Oligosaccharide Synthesis Based on a Hop-On/Off Carrier.

Yingle Feng, Jingjing Wu, Guosong Chen*, andYonghai Chai*.Org. Lett.2020, 22,2564−2568.

2019

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

Yujia Zu†, Chenglin Cai†, Jingyuan Sheng, Lili Cheng, Yingle Feng, Shengyong Zhang, Qi Zhang*, andYonghai Chai*.Org. Lett.2019,21, 8270−8274.

13. Stereoselective β‐Mannosylation with 2,6‐Lactone‐bridged Thiomannosyl Donor by Remote Acyl Group Participation.

Huanfang Xu†, Long Chen†, Qi Zhang, Yingle Feng, Yujia Zu, andYonghai Chai*.Chem. - Asian J.2019, 14,1424-1428.

12. Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Brønsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement.

Jincai Wang, Chuqiao Deng, Qi Zhang*, andYonghai Chai*.Org. Lett.2019,21, 1103−1107.

11. Diverse synthesis of pyrimido[1,2-a]benzimidazoles and imidazo[2,1-b]benzothiazoles via CuI-catalyzed decarboxylic multicomponent reactions of heterocyclic azoles, aldehydes and alkynecarboxylic acids.

Jiarong Wu† , Huan Luo†, Tao Wang , Huaming Sun , Qi Zhang*, andYonghai Chai*.Tetrahedron2019,75, 1052-1063.

2018

10. Organo-Catalyzed Regio- and Geometry-Specific Construction of β-Hydroxyl-α-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications.

Yonghai Chai*, JinJin Zhou, Yanbin Wu, Yingle Feng, Panru Wang, Yange Chen, Xinying Wang, Beibei Zhao, and Qi Zhang*.J. Org. Chem.2018,83, 10476−10486.

2017

9. Metal‐Free Synthesis of Pyrazoles from 1,3‐Diarylpropenes and Hydrazines via Multiple Inter‐/Intramolecular C–H Aminations.

Li Tang, Minyan Ma, Qi Zhang*, Huan Luo, Tao Wang, andYonghai Chai*.Adv. Synth. Catal.2017,359, 2610 –2620.

8. Synthesis of the ABC Tricyclic System of Daphnicyclidin A.

Jianlong Li,† Hongwei Shi,† Qi Wang,Yonghai Chai, and Jun Yang*.Org. Lett.2017,19, 1497−1499.

2016

7. Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles.

Qi Zhang*, Linjing Zhang, Chaojun Tang, Huan Luo, Xuediao Cai, andYonghai Chai*.Tetrahedron2016,72, 6935-6942.

6. Transition‐Metal‐Free Synthesis of 1,3‐Butadiene‐Containing π‐Conjugated Polymers.

Xuediao Cai,* Yating Liu, Tian Lu, Rui Yang, Chuxin Luo, Qi Zhang, andYonghai Chai*.Macromol. Rapid Commun.2016,37, 2005−2010.

5. Biodegradation of patulin by a Byssochlamys nivea strain.

Xiaorui Zhang, Yurong Guo*, Yu Ma,Yonghai Chai, and Yangyang Li.Food Control,2016,64, 142-150.

2015

4. Efficient Large Scale Syntheses of 3-Deoxy-d-manno-2-octulosonic acid (Kdo) and Its Derivatives.

Yingle Feng, Jie Dong, Fangyuan Xu, Aiyun Liu, Li Wang, Qi Zhang, andYonghai Chai*.Org. Lett.2015,17, 2388−2391.

3. Mild and Selective Deprotection of tert-Butyl(dimethyl)silyl Ethers with Catalytic­ Amounts of Sodium Tetrachloroaurate(III) Dihydrate.

Qi Zhang*, Xiuqin Kang, Lei Long, Lijuan Zhu, andYonghai Chai*.Synthesis2015,47, 55–64.

2. Diphenylprolinol silyl ether-derived thioureas as highly efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes.

Chunyan He, Xiaochen Ren, Yingle Feng,Yonghai Chai*, Shengyong Zhang, and Weiping Chen*.Tetrahedron Lett.2015,56,4036–4038.

1. Novel ferrocene-based bifunctional amine–thioureas for asymmetric Michael addition of acetylacetone to nitroolefins.

Xiaochen Ren, Chunyan He, Yingle Feng,Yonghai Chai*, Wei Yao, Weiping Chen, and Shengyong Zhang*.Org. Biomol. Chem.2015,13, 5054-5060.

专利：

（1）双侧链苄基型氟载体及其应用。 柴永海；吴晶晶；冯颖乐；刘爱云；张琦。 专利号： ZL 2014105380632.2

（2）一种合成萘环衍生物和苯并杂环类化合物的方法。 柴永海；康磊；张敏；冯颖乐；吴晏兵；张琦。专利号：ZL 2014 10763995.7

（3）3-脱氧-D-甘露-2-辛酮糖酸铵盐的合成方法。柴永海；张琦；徐芳园；董洁；冯颖乐。 ZL 201210558246.1

（4）一种1，5-烯炔醇类化合物的合成方法及其应用。柴永海；祖瑜佳；盛靖园；程丽丽； 张琦。ZL 201410810658.9

（5）一种合成a-烯基-b-羟基酯类化合物的方法。柴永海；吴晏兵；周瑾瑾；康磊；冯颖乐； 陈艳鸽；王盼茹；徐阳；张琦。ZL 201410819813.3

（6）一种中药水蛭提取物及其用途。柴永海 ; 杨培民 ; 刘国飞 ; 邱学伟 ; 代龙 。ZL 201310097031.9

（7）棒曲霉素的制备方法。张晓瑞 ; 郭玉蓉 ; 柴永海 ; 马瑜。 ZL 201410408772.9

（8）扩展青霉FP2菌株及其应用。张晓瑞 ; 郭玉蓉 ; 马瑜 ; 柴永海。ZL 201410408759.3