Stereoselective glycosylation of exo-glycals accelerated by Ferrier-type rearrangement.
[reaction: see text] Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.
Lin
Hui-Chang
HC
Institute of Biological Chemistry, Academia Sinica, No. 128, Academia Road Section 2, Nan-Kang, Taipei, 11529, Taiwan.
Yang
Wen-Bin
WB
Gu
Yu-Feng
YF
Chen
Chen-Yin
CY
Wu
Chung-Yi
CY
Lin
Chun-Hung
CH
D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure
D006001:Glycoconjugates; D006027:Glycosides