Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

Mithila D. Bandara; Jagodige P. Yasomanee; Nigam P. Rath; Christian M. Pedersen; Mikael Bols; Alexei V. Demchenko

doi:10.1039/C6OB02498J

Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

Mithila D. Bandara, Jagodige P. Yasomanee, Nigam P. Rath, Christian M. Pedersen, Mikael Bols, Alexei V. Demchenko

University of Missouri-St. Louis

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

Abstract

A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.

Original language	American English
Journal	Organic and Biomolecular Chemistry
Volume	15
DOIs	https://doi.org/10.1039/C6OB02498J
State	Published - Jan 1 2017

Disciplines

Organic Chemistry
Biochemistry
Biochemical and Biomolecular Engineering

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Cite this

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abstract = " A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.",

author = "Bandara, {Mithila D.} and Yasomanee, {Jagodige P.} and Rath, {Nigam P.} and Pedersen, {Christian M.} and Mikael Bols and Demchenko, {Alexei V.}",

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doi = "10.1039/C6OB02498J",

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T1 - Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

AU - Bandara, Mithila D.

AU - Yasomanee, Jagodige P.

AU - Rath, Nigam P.

AU - Pedersen, Christian M.

AU - Bols, Mikael

AU - Demchenko, Alexei V.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.

AB - A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.

U2 - 10.1039/C6OB02498J

DO - 10.1039/C6OB02498J

M3 - Article

VL - 15

JO - Organic and Biomolecular Chemistry

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