Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride

An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthalic anhydride resulted in few to no undesired s...

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Bibliographic Details
Published in:Tetrahedron letters 2010-12, Vol.51 (48), p.6250-6254
Main Authors: Baek, Ju Yuel, Lee, Bo-Young, Pal, Rita, Lee, Won-Yong, Kim, Kwan Soo
Format: Article
Language:English
Subjects:
3-Fluorophthalic anhydride
Activation
Anhydrides
Esters
Glycosyl fluorophthalate
Glycosylation
Nuclear magnetic resonance
Phthalic anhydride
Sugars
Tetrahedrons
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Summary:An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been developed. The present glycosylation utilizing 3-fluorophthalic anhydride resulted in few to no undesired self-condensed esters than the glycosylation using phthalic anhydride. Intermediates in the present glycosylation were identified by an NMR study.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.09.064