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Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl3)

文献类型：期刊论文

作者Chen, Shuangyuan7,8; Wei, Feifei7,8; Cheng, Xinqiang7; Luo, Ying4,7; Meng, Fancui3; Zhang, Yuanwen2,7; Huang, Wenqian5,6,7; Lv, Jun5,6,7; Pan, Hong1; Wu, Qingqing7
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2024-03-13
页码16
ISSN号0022-3263
DOI10.1021/acs.joc.4c00026
通讯作者Pan, Hong(panhongdz@126.com) ; Wu, Qingqing(wuqingqing@zidd.ac.cn) ; Zhao, Guilong(zhao_guilong@126.com)
英文摘要A general approach for regioselective deacetylation at sugar 3-OH of peracetylated 6-deoxy-C-glucopyranosides mediated by BCl3 was developed. The approach could be extended to other sugar-derived 6-deoxy-C-glycopyranosides, such as those derived from mannose, galactose, and rhamnose, with deacetylation occurring at varied sugar hydroxyl groups, and further extended to 4-deoxy-C-glucopyranosides with deacetylation occurring at sugar 3-OH. The approach would enable access to synthetically challenging carbohydrate derivatives. A possible mechanism of the regioselectivity was proposed.
WOS关键词FULLY ACYLATED PURINE ; SITE-SELECTIVE FUNCTIONALIZATION ; CARBOHYDRATE-DERIVATIVES ; PARTIAL PROTECTION ; PYRIMIDINE RIBONUCLEOSIDES ; SUGAR ; DEACYLATION ; 1-O-DEACETYLATION ; 2'-O-DEACYLATION ; DEPROTECTION
资助项目Zhongshan Municipal Natural Science Foundation[2021A1515010197] ; Zhongshan Municipal Natural Science Foundation[2023A1515012259] ; Guangdong Basic and Applied Basic Research Foundation[200805173640573] ; Guangdong Basic and Applied Basic Research Foundation[210730214049987] ; Guangdong Basic and Applied Basic Research Foundation[221018194369472] ; Zhongshan Municipal Natural Science Foundation[CXTD2022011] ; Creative Research Group of Zhongshan City (Lingnan Pharmaceutical Research and Innovation team)[23YYJC0002] ; Dazhou Applied Basic Research Foundation
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001184774000001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/310151]  
专题中国科学院上海药物研究所
通讯作者Pan, Hong; Wu, Qingqing; Zhao, Guilong
作者单位1.Dazhou Vocat & Tech Coll, Sch Intelligent Med Technol, Dazhou 635001, Peoples R China
2.Guangdong Pharmaceut Univ, Sch Chinese Med Resource, Guangzhou 510006, Peoples R China
3.Tianjin Inst Pharmaceut Res, Natl Key Lab Druggabil Evaluat & Systemat Translat, Tianjin 300301, Peoples R China
4.Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Peoples R China
5.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
6.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
7.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
8.Guizhou Med Univ, Coll Pharm, Guiyang 561113, Peoples R China
推荐引用方式
GB/T 7714		 Chen, Shuangyuan,Wei, Feifei,Cheng, Xinqiang,et al. Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl3)[J]. JOURNAL OF ORGANIC CHEMISTRY,2024:16.
APA Chen, Shuangyuan.,Wei, Feifei.,Cheng, Xinqiang.,Luo, Ying.,Meng, Fancui.,...&Zhao, Guilong.(2024).Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl3).JOURNAL OF ORGANIC CHEMISTRY,16.
MLA Chen, Shuangyuan,et al."Regioselective Deacetylation of Peracetylated Deoxy-C-glycopyranosides by Boron Trichloride (BCl3)".JOURNAL OF ORGANIC CHEMISTRY (2024):16.

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来源：上海药物研究所

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