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 Marcus 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 Marcus Pedersen, Mikael Bols, Alexei V. Demchenko

Department of Chemistry

10 Citations (Scopus)

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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

Original language	English
Journal	Organic & Biomolecular Chemistry
Volume	15
Issue number	3
Pages (from-to)	559-563
Number of pages	5
ISSN	1477-0520
DOIs	https://doi.org/10.1039/c6ob02498j
Publication status	Published - 2017

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10.1039/c6ob02498jLicence: CC BY

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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 Marcus} and Mikael Bols and Demchenko, {Alexei V.}",

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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 Marcus

AU - Bols, Mikael

AU - Demchenko, Alexei V.

PY - 2017

Y1 - 2017

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 - Journal article

C2 - 27942674

SN - 1470-4358

VL - 15

SP - 559

EP - 563

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

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