A facile method for synthesis of 1,2-oxazoline derivative of N-acetylglucosamine promoted by potassium fluoride

Shin Ichiro Shoda; Ryuko Izumi; Masako Suenaga; Kenji Saito; Masaya Fujita

doi:10.1246/cl.2002.150

A facile method for synthesis of 1,2-oxazoline derivative of N-acetylglucosamine promoted by potassium fluoride

Shin Ichiro Shoda, Ryuko Izumi, Masako Suenaga, Kenji Saito, Masaya Fujita

ENG - Biomolecular Engineering

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

10 Citations (Scopus)

Abstract

A potassium fluoride-promoted intramolecular cyclization reaction of 2-acetamido-2-deoxy-α-D-glucopyranosyl chloride took place smoothly, giving the corresponding 1,2-oxazoline derivative in good yield. Potassium fluoride behaves as a nucleophile for anomerization of the glycosyl chloride as well as an acid captor to scavenge the protonic acid liberated. This is an extremely practical method for preparation of sugar oxazoline derivatives with simple experimental procedures.

Original language	English
Pages (from-to)	150-151
Number of pages	2
Journal	Chemistry Letters
Issue number	2
DOIs	https://doi.org/10.1246/cl.2002.150
Publication status	Published - 2002 Feb 5

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2002.150

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AU - Shoda, Shin Ichiro

AU - Izumi, Ryuko

AU - Suenaga, Masako

AU - Saito, Kenji

AU - Fujita, Masaya

PY - 2002/2/5

Y1 - 2002/2/5

N2 - A potassium fluoride-promoted intramolecular cyclization reaction of 2-acetamido-2-deoxy-α-D-glucopyranosyl chloride took place smoothly, giving the corresponding 1,2-oxazoline derivative in good yield. Potassium fluoride behaves as a nucleophile for anomerization of the glycosyl chloride as well as an acid captor to scavenge the protonic acid liberated. This is an extremely practical method for preparation of sugar oxazoline derivatives with simple experimental procedures.

AB - A potassium fluoride-promoted intramolecular cyclization reaction of 2-acetamido-2-deoxy-α-D-glucopyranosyl chloride took place smoothly, giving the corresponding 1,2-oxazoline derivative in good yield. Potassium fluoride behaves as a nucleophile for anomerization of the glycosyl chloride as well as an acid captor to scavenge the protonic acid liberated. This is an extremely practical method for preparation of sugar oxazoline derivatives with simple experimental procedures.

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A facile method for synthesis of 1,2-oxazoline derivative of N-acetylglucosamine promoted by potassium fluoride

Abstract

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