Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 40, Pages 13402-13407Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08305
Keywords
-
Categories
Funding
- National Natural Science Foundation of China [21272082, 21402055, 21472054]
- State Key Laboratory of Bio-organic and Natural Products Chemistry [SKLBNPC13425]
- Natural Science Funds of Hubei Province for Distinguished Young Scholars [2015CFA035]
- Thousand Talents Program Young Investigator Award
- Wuhan Creative Talent Development Fund
- Fundamental Research Funds for the Central Universities
- Huazhong University of Science and Technology [2014ZZGH015]
Ask authors/readers for more resources
S-glycosides, S-2-(2-propylthio)benzyl (SPTB) glycosides, were converted to the corresponding oxidized glycosyl donors, S-2-(2-propylsulfinyl)benzyl (SPSB) glycosides, by simple and selective oxidation. Treatment of disarmed SPSB donor and various acceptors with triflic anhydride provided the desired glycosides in good to excellent yields. Meanwhile, observation of thiosulfinate, thiosulfonate, and disulfide suggested that the leaving group was activated via an interrupted Pummerer reaction. The disarmed SPSB thioglycosyl donors could be selectively activated in the presence of various thioglycosides with remote activation mode. Finally, two natural hepatoprotective glycosides, Leonoside E and Leonuriside B, were efficiently synthesized in a convergent manner with this newly developed method.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available