Stereoselective glycosylation of exo-glycals by microwave-assisted Ferrier rearrangement | Zendy

HuiChang Lin | Zendy; ChihChun Chang | Zendy; Jiayi Chen | Zendy; ChunHung Lin | Zendy

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Stereoselective glycosylation of exo-glycals by microwave-assisted Ferrier rearrangement

Author(s) -

HuiChang Lin,

ChihChun Chang,

Jiayi Chen,

ChunHung Lin

Publication year - 2005

Publication title -

tetrahedron asymmetry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.396

H-Index - 107

eISSN - 1362-511X

pISSN - 0957-4166

DOI - 10.1016/j.tetasy.2004.11.044

Subject(s) - stereoselectivity , glycosyl , chemistry , glycosylation , yield (engineering) , glycoside , lewis acids and bases , stereochemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy

exo -Glycosyl carbonates were shown to be efficient glycosyl donors in microwave-assisted glycosylation. In these reactions α-glycosyl additions occurred with excellent stereoselectivity and were complete in 4–8 min with 75–92% yield. Interestingly exo -glycals were found to have higher activity than endo -glycals and common glycosides, the reactions of which can be improved by the addition of Lewis acid to result in a higher yield and enhanced stereoselectivity.

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