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

研究成果: Article › 査読

10 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	150-151
ページ数	2
ジャーナル	Chemistry Letters
号	2
DOI	https://doi.org/10.1246/cl.2002.150
出版ステータス	Published - 2002 2月 5
外部発表	はい

ASJC Scopus subject areas

化学 (全般)

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10.1246/cl.2002.150

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AU - Shoda, Shin Ichiro

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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

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