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Stereospecific synthesis and rearrangement of 22S-23-acetylsapogenins

文献类型：期刊论文

作者Lu, Yi-hong1,2; Xie, Yang3; Hu, Pei2; Sun, Zhao-lin2; Li, Zhi-xiong2; Huang, Cheng-gang1,2
刊名STEROIDS
出版日期2020-08-01
卷号160页码:9
关键词22-epi-steroid sapogenins BF3 center dot Et2O-catalysed rearrangement Dihydropyran furostanol frameworks X-ray diffraction
ISSN号0039-128X
DOI10.1016/j.steroids.2020.108655
通讯作者Li, Zhi-xiong(zxli0715@126.com) ; Huang, Cheng-gang(cghsimm@126.com)
英文摘要The BF3 center dot Et2O-catalysed acetolysis of steroid sapogenins diosgenin, sarsasapogenin and tigogenin in dichloromethane as the solvent instead of acetic anhydride afforded (20S)- and (20R)-22,26-epoxycholestanes (compounds 1 and 2). 22S-23-Acetylsapogenins (compounds 4) were synthesized stereospecifically from 20R-22,26-epoxycholestanes (compounds 2) in good yield. The rearrangement of 22S-23-acetylsapogenins (compounds 4) afforded novel disubstituted dihydropyran furostanol frameworks. Exhaustive NMR characterization of the obtained compounds is provided. Additionally, the structures of the critical compounds (6a and 7a) were unequivocally confirmed by single crystal X-ray diffraction studies.
WOS关键词STEROIDAL SAPONINS ; SIDE-CHAIN ; EPIMERIZATION ; ISOMERIZATION ; SAPOGENINS ; C-22
资助项目National Natural Science Foundation of China[1803828] ; National Science and Technology Major Project of the Ministry of Science and Technology of China[2019ZX09201001-001-003] ; Shanghai Science and Technology Development Funds[18401931300] ; Youth Innovation Promotion Association of Chinese Academy of Sciences[2019280]
WOS研究方向Biochemistry & Molecular Biology ; Endocrinology & Metabolism
语种英语
WOS记录号WOS:000545322000006
出版者ELSEVIER SCIENCE INC
源URL[http://119.78.100.183/handle/2S10ELR8/291960]  
专题中国科学院上海药物研究所
通讯作者Li, Zhi-xiong; Huang, Cheng-gang
作者单位1.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, 501 Haike Rd, Shanghai 201203, Peoples R China
3.Zhejiang Univ, Dept Chem, 866 Yuhangtang Rd, Hangzhou 310027, Peoples R China
推荐引用方式
GB/T 7714		 Lu, Yi-hong,Xie, Yang,Hu, Pei,et al. Stereospecific synthesis and rearrangement of 22S-23-acetylsapogenins[J]. STEROIDS,2020,160:9.
APA Lu, Yi-hong,Xie, Yang,Hu, Pei,Sun, Zhao-lin,Li, Zhi-xiong,&Huang, Cheng-gang.(2020).Stereospecific synthesis and rearrangement of 22S-23-acetylsapogenins.STEROIDS,160,9.
MLA Lu, Yi-hong,et al."Stereospecific synthesis and rearrangement of 22S-23-acetylsapogenins".STEROIDS 160(2020):9.

入库方式： OAI收割

来源：上海药物研究所

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