General synthesis of sugar-derived azepane nitrones: Precursors of azepane iminosugars

Wen Bo Zhao; Shinpei Nakagawa; Atsushi Kato; Isao Adachi; Yue Mei Jia; Xiang Guo Hu; George W.J. Fleet; Francis X. Wilson; Graeme Horne; Akihide Yoshihara; Ken Izumori; Chu Yi Yu

doi:10.1021/jo400130p

General synthesis of sugar-derived azepane nitrones: Precursors of azepane iminosugars

Wen Bo Zhao, Shinpei Nakagawa, Atsushi Kato, Isao Adachi, Yue Mei Jia, Xiang Guo Hu, George W.J. Fleet, Francis X. Wilson, Graeme Horne, Akihide Yoshihara, Ken Izumori, Chu Yi Yu^*

^*Corresponding author for this work

Hospital Pharmacy

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

38 Scopus citations

Abstract

A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

Original language	English
Pages (from-to)	3208-3221
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	78
Issue number	7
DOIs	https://doi.org/10.1021/jo400130p
State	Published - 2013/04/05

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo400130p

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title = "General synthesis of sugar-derived azepane nitrones: Precursors of azepane iminosugars",

abstract = "A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.",

author = "Zhao, {Wen Bo} and Shinpei Nakagawa and Atsushi Kato and Isao Adachi and Jia, {Yue Mei} and Hu, {Xiang Guo} and Fleet, {George W.J.} and Wilson, {Francis X.} and Graeme Horne and Akihide Yoshihara and Ken Izumori and Yu, {Chu Yi}",

year = "2013",

month = apr,

day = "5",

doi = "10.1021/jo400130p",

language = "英語",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - General synthesis of sugar-derived azepane nitrones

T2 - Precursors of azepane iminosugars

AU - Zhao, Wen Bo

AU - Nakagawa, Shinpei

AU - Kato, Atsushi

AU - Adachi, Isao

AU - Jia, Yue Mei

AU - Hu, Xiang Guo

AU - Fleet, George W.J.

AU - Wilson, Francis X.

AU - Horne, Graeme

AU - Yoshihara, Akihide

AU - Izumori, Ken

AU - Yu, Chu Yi

PY - 2013/4/5

Y1 - 2013/4/5

N2 - A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

AB - A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

UR - http://www.scopus.com/inward/record.url?scp=84875919759&partnerID=8YFLogxK

U2 - 10.1021/jo400130p

DO - 10.1021/jo400130p

M3 - 学術論文

C2 - 23458237

AN - SCOPUS:84875919759

SN - 0022-3263

VL - 78

SP - 3208

EP - 3221

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

General synthesis of sugar-derived azepane nitrones: Precursors of azepane iminosugars

Abstract

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