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59949091621
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2O to 15 would give a glycosyl triflate mixed anhydride, and then upon addition of Deoxofluor, the triflate would be displaced by the fluoride anion of Deoxofluor to provide a glycosyl carboxy fluoride intermediate. Finally, HF/pyridine would facilitate the lactonization of the carboxy fluoride to generate a glycosyl oxocarbenium ion, which would readily react with fluoride ion to afford glycosyl fluoride 18. In fact, we were able to isolate the glycosyl carboxy fluoride intermediate.
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2O to 15 would give a glycosyl triflate mixed anhydride, and then upon addition of Deoxofluor, the triflate would be displaced by the fluoride anion of Deoxofluor to provide a glycosyl carboxy fluoride intermediate. Finally, HF/pyridine would facilitate the lactonization of the carboxy fluoride to generate a glycosyl oxocarbenium ion, which would readily react with fluoride ion to afford glycosyl fluoride 18. In fact, we were able to isolate the glycosyl carboxy fluoride intermediate.
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59949087286
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4 as the promoter for glycosyl fluoride, see: Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
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4 as the promoter for glycosyl fluoride, see: Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
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