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

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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