Trifluoroacetamido substituted sialyl donors for the preparation of sialyl galactosides

Cristina De Meo; Alexei V. Demchenko; Geert Jan Boons

Trifluoroacetamido substituted sialyl donors for the preparation of sialyl galactosides

Cristina De Meo, Alexei V. Demchenko, Geert Jan Boons

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

An efficient method for the direct synthesis of sialyl galactosides was described using glycosyl donor bearing a trifluoroacetamido group. It was found that glycosidation of 5-n-trifluoroacetyle neuraminyl donor with the range of D-galactosyl acceptors gave high yields and α-stereoselectivities for the preparation of Neu5Ac(2,3)Gal derivatives. In the synthesis procedure, mixtures of anomers were obtained. Modest stereoselectivities were also obtained when sialyl donor was glycosidated with the C6 hydroxyl of D-galactosides.

Original language	English
Pages (from-to)	131-134
Number of pages	4
Journal	Australian Journal of Chemistry
Volume	55
Issue number	1-2
Publication status	Published - 1 Jan 2002
Externally published	Yes

Cite this

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abstract = "An efficient method for the direct synthesis of sialyl galactosides was described using glycosyl donor bearing a trifluoroacetamido group. It was found that glycosidation of 5-n-trifluoroacetyle neuraminyl donor with the range of D-galactosyl acceptors gave high yields and α-stereoselectivities for the preparation of Neu5Ac(2,3)Gal derivatives. In the synthesis procedure, mixtures of anomers were obtained. Modest stereoselectivities were also obtained when sialyl donor was glycosidated with the C6 hydroxyl of D-galactosides.",

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AU - Demchenko, Alexei V.

AU - Boons, Geert Jan

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Y1 - 2002/1/1

N2 - An efficient method for the direct synthesis of sialyl galactosides was described using glycosyl donor bearing a trifluoroacetamido group. It was found that glycosidation of 5-n-trifluoroacetyle neuraminyl donor with the range of D-galactosyl acceptors gave high yields and α-stereoselectivities for the preparation of Neu5Ac(2,3)Gal derivatives. In the synthesis procedure, mixtures of anomers were obtained. Modest stereoselectivities were also obtained when sialyl donor was glycosidated with the C6 hydroxyl of D-galactosides.

AB - An efficient method for the direct synthesis of sialyl galactosides was described using glycosyl donor bearing a trifluoroacetamido group. It was found that glycosidation of 5-n-trifluoroacetyle neuraminyl donor with the range of D-galactosyl acceptors gave high yields and α-stereoselectivities for the preparation of Neu5Ac(2,3)Gal derivatives. In the synthesis procedure, mixtures of anomers were obtained. Modest stereoselectivities were also obtained when sialyl donor was glycosidated with the C6 hydroxyl of D-galactosides.

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M3 - Article

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EP - 134

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

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ER -

Trifluoroacetamido substituted sialyl donors for the preparation of sialyl galactosides

Abstract

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