Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group

doi:10.1016/j.carres.2008.09.001

Carbohydrate Research

Volume 343, Issue 17, 24 November 2008, Pages 2992-2996

Dedicated to Professor Yongzheng Hui on the occasion of his 70th birthday

https://doi.org/10.1016/j.carres.2008.09.001 Get rights and content

Abstract

Fructofuranosyl trifluoroacetimidate 3 was demonstrated to be an effective glycosyl donor that exhibited good α-selectivity and good yield in fructosylation reactions. The reaction proceeds via neighboring group participation, which was proved by the isolation of a stable allylic orthoester intermediate.

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Section snippets

General methods

Solvents were purified in the usual way. Thin layer chromatography (TLC) was performed on precoated plates of Silica Gel HF254 (0.5 mm, Yantai, China). Flash column chromatography was performed on Silica Gel H (10–40 μm, Yantai, China). Optical rotations were determined with a Perkin–Elmer Model 241 MC polarimeter. IR spectra were recorded on a NICOLET FTIR-360 spectrometer. NMR spectra were recorded on a Bruker AM 300 spectrometer with Me₄Si as the internal standard. Mass spectra were recorded

Acknowledgments

This work was supported by the National Natural Science Foundation of China (29925203) and the Committee of Science and Technology of Shanghai (02QMA1401). F.L. thanks the Open Foundation of State Key Lab of Biochemistry and Natural Products Chemistry, SIOC.

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Citation Excerpt :
Yu and co-workers recently developed N-phenyl trifluoroacetimidate donor,25,26 which was successfully applied in direct sialylation, glycosylation of primary amides, hydroxamic acid, deoxysugars, and several total synthesis.27 In 2008, we reported an efficient fructofuranosylation employing N-phenyl trifluoroacetimidate donor.28 We further investigate its application in fructopyranosides synthesis.

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NoteSynthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group

Abstract

Graphical abstract

Section snippets

General methods

Acknowledgments

Microbiol. Lett.

Biochim. Biophys. Acta

J. Nutr.

Anticancer Res.

Chem. Res. Toxicol.

J. Org. Chem.

Aust. J. Chem.

J. Am. Chem. Soc.

Liebigs Ann. Org. Bioorg. Chem.

Tetrahedron Lett.

Tetrahedron Lett.

J. Org. Chem.

Liebigs Ann. Chem.

Note
Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group