Citation: Jian Rong Zhu, Ji Jun Xue, Wen Ze Li, Xue Song Chen, Ying Li. Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases[J]. Chinese Chemical Letters, ;2010, 21(3): 273-276. doi: 10.1016/j.cclet.2009.11.049 shu

Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases

a The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China;
b Zhejiang Jiuzhou Pharmaceutical Co. Ltd., 99 Waisha Rd., Jiaojiang Taizhou City, Zhejiang 318000, China

Received Date: 15 June 2009

Fund Project: We are grateful to Dr. Qiang Gao (Shanghai Haoyuan Express Chemical Company Ltd. Of China) for his donation of actin and their helpful advice and discussions. Project No. 20672050 supported by the National Natural Science Foundation of China.

Simple organic nitrogen bases, such as Et₃N, pyridine, DBU, etc., were found to be convenient and useful reagents for deprotection of TBDMS groups on acidic hydroxyl groups. The efficiency of these bases has an apparent order: 1°amine > 2°amine > 3°amine and aliphatic base>aromatic base. In aqueous DMSO and at room temperature, phenolic TBDMS ethers were removed selectively in the presence of alcoholic TBDMS ethers. And catalytic base can make these reactions complete. This method is high-yielding, fast, clean, safe and cost-effective.
- Selective cleavage,
- Phenolic tert-butyldimethylsilyl ethers,
- Organic nitrogen bases
1. [1]
  Rui PAN , Yuting MENG , Ruigang XIE , Daixiang CHEN , Jiefa SHEN , Shenghu YAN , Jianwu LIU , Yue ZHANG . Selective electrocatalytic reduction of Sn(Ⅳ) by carbon nitrogen materials prepared with different precursors. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1015-1024. doi: 10.11862/CJIC.20230433
2. [2]
  Xiaxia Xing , Xiaoyu Chen , Zhenxu Li , Xinhua Zhao , Yingying Tian , Xiaoyan Lang , Dachi Yang . Polyethylene imine functionalized porous carbon framework for selective nitrogen dioxide sensing with smartphone communication. Chinese Chemical Letters, 2024, 35(9): 109230-. doi: 10.1016/j.cclet.2023.109230
3. [3]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
4. [4]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
5. [5]
  Yuqing Ding , Zhiying Yi , Zhihui Wang , Hongyu Chen , Yan Zhao . Liquid nitrogen post-treatment for improved aggregation and electrical properties in organic semiconductors. Chinese Chemical Letters, 2024, 35(12): 109918-. doi: 10.1016/j.cclet.2024.109918
6. [6]
  Jie ZHANG , Xin LIU , Zhixin LI , Yuting PEI , Yuqi YANG , Huimin LI , Zhiqiang LIU . Assembling a luminescence silencing system based on post-synthetic modification strategy: A highly sensitive and selective turn-on metal-organic framework probe for ascorbic acid detection. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 823-833. doi: 10.11862/CJIC.20230310
7. [7]
  Kezhen Qi , Shu-yuan Liu , Ruchun Li . Selective dissolution for stabilizing solid electrolyte interphase. Chinese Chemical Letters, 2024, 35(5): 109460-. doi: 10.1016/j.cclet.2023.109460
8. [8]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
9. [9]
  Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
10. [10]
  Zhipeng Wan , Hao Xu , Peng Wu . Selective oxidation using in-situ generated hydrogen peroxide over titanosilicates. Chinese Journal of Structural Chemistry, 2024, 43(6): 100298-100298. doi: 10.1016/j.cjsc.2024.100298
11. [11]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
12. [12]
  Tianbo Jia , Lili Wang , Zhouhao Zhu , Baikang Zhu , Yingtang Zhou , Guoxing Zhu , Mingshan Zhu , Hengcong Tao . Modulating the degree of O vacancy defects to achieve selective control of electrochemical CO₂ reduction products. Chinese Chemical Letters, 2024, 35(5): 108692-. doi: 10.1016/j.cclet.2023.108692
13. [13]
  Yang Liu , Yan Liu , Kaiyin Yang , Zhiruo Zhang , Wenbo Zhang , Bingyou Yang , Hua Li , Lixia Chen . A selective HK2 degrader suppresses SW480 cancer cell growth by degrading HK2. Chinese Chemical Letters, 2024, 35(8): 109264-. doi: 10.1016/j.cclet.2023.109264
14. [14]
  Huan Yao , Jian Qin , Yan-Fang Wang , Song-Meng Wang , Liu-Huan Yi , Shi-Yao Li , Fangfang Du , Liu-Pan Yang , Li-Li Wang . Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay. Chinese Chemical Letters, 2024, 35(6): 109154-. doi: 10.1016/j.cclet.2023.109154
15. [15]
  Shuqi Yu , Yu Yang , Keisuke Kuroda , Jian Pu , Rui Guo , Li-An Hou . Selective removal of Cr(Ⅵ) using polyvinylpyrrolidone and polyacrylamide co-modified MoS₂ composites by adsorption combined with reduction. Chinese Chemical Letters, 2024, 35(6): 109130-. doi: 10.1016/j.cclet.2023.109130
16. [16]
  Xin Li , Xuan Ding , Junkun Zhou , Hui Shi , Zhenxi Dai , Jiayi Liu , Yongcun Ma , Penghui Shao , Liming Yang , Xubiao Luo . Utilizing synergistic effects of bifunctional polymer hydrogel PAM-PAMPS for selective capture of Pb(Ⅱ) from wastewater. Chinese Chemical Letters, 2024, 35(7): 109158-. doi: 10.1016/j.cclet.2023.109158
17. [17]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
18. [18]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
19. [19]
  Shuo Li , Qianfa Liu , Lijun Mao , Xin Zhang , Chunju Li , Da Ma . Benzothiadiazole-based water-soluble macrocycle: Synthesis, aggregation-induced emission and selective detection of spermine. Chinese Chemical Letters, 2024, 35(11): 109791-. doi: 10.1016/j.cclet.2024.109791
20. [20]
  Jichun Li , Zhengren Wang , Yu Deng , Hongxiu Yu , Yonghui Deng , Xiaowei Cheng , Kaiping Yuan . Construction of mesoporous silica-implanted tungsten oxides for selective acetone gas sensing. Chinese Chemical Letters, 2024, 35(11): 110111-. doi: 10.1016/j.cclet.2024.110111

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(499)
HTML views(5)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return