(1R)-2,3,4,6-Tetra-O-benzyl-1-C-allyl-1-deoxy-1-C-(2-thiazolyl)-D-galactopyranose DOI Creative Commons
Clark Ferrari,

Alessandro Dondoni,

Alberto Marra

et al.

Molbank, Journal Year: 2025, Volume and Issue: 2025(1), P. M1949 - M1949

Published: Jan. 8, 2025

We have previously reported that thiazolylketol acetates, synthesized by the addition of 2-lithiothiazole to sugar lactones followed acetylation, are efficient glycosyl donors affording O-, N-, P-, and C-glycosides. After first example C-glycosidation recently described us, we report here on unexpected outcome reaction a acetate with allyltrimethylsilane in presence trimethylsilyl triflate. The obtained intermediate, an intramolecular N-thiazolium salt, could be stereoselectively converted into desired allyl C-thiazolylketoside.

Language: Английский

(1R)-2,3,4,6-Tetra-O-benzyl-1-C-allyl-1-deoxy-1-C-(2-thiazolyl)-D-galactopyranose DOI Creative Commons
Clark Ferrari,

Alessandro Dondoni,

Alberto Marra

et al.

Molbank, Journal Year: 2025, Volume and Issue: 2025(1), P. M1949 - M1949

Published: Jan. 8, 2025

We have previously reported that thiazolylketol acetates, synthesized by the addition of 2-lithiothiazole to sugar lactones followed acetylation, are efficient glycosyl donors affording O-, N-, P-, and C-glycosides. After first example C-glycosidation recently described us, we report here on unexpected outcome reaction a acetate with allyltrimethylsilane in presence trimethylsilyl triflate. The obtained intermediate, an intramolecular N-thiazolium salt, could be stereoselectively converted into desired allyl C-thiazolylketoside.

Language: Английский

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