Bi(OTf)                         3                         -mediated intramolecular epoxide opening for bicyclic azepane synthesis

Sha Zhu; Anh Tuan Tran; Yuki Hirokami; Geoffrey Gontard; Omar Khaled; Yongmin Zhang; Atsushi Kato; Yves Blériot; Matthieu Sollogoub

doi:10.1080/07328303.2019.1581887

Bi(OTf) ₃ -mediated intramolecular epoxide opening for bicyclic azepane synthesis

Sha Zhu, Anh Tuan Tran, Yuki Hirokami, Geoffrey Gontard, Omar Khaled, Yongmin Zhang, Atsushi Kato, Yves Blériot, Matthieu Sollogoub^*

^*Corresponding author for this work

Hospital Pharmacy

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

1 Scopus citations

Abstract

While an epoxide on a sugar-derived aziridine studying was opened, an unexpected formation of bicyclic compounds was observed. The structure of these bicycles depended on the nature of the protecting group on the nitrogen atom of the aziridine. These compounds appeared to be weak glycosidase inhibitors.

Original language	English
Pages (from-to)	139-149
Number of pages	11
Journal	Journal of Carbohydrate Chemistry
Volume	38
Issue number	2
DOIs	https://doi.org/10.1080/07328303.2019.1581887
State	Published - 2019/02/12

Keywords

Azasugar
Azepane
Glycosidase inhibitors

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

Access to Document

10.1080/07328303.2019.1581887

Cite this

Zhu, S., Tran, A. T., Hirokami, Y., Gontard, G., Khaled, O., Zhang, Y., Kato, A., Blériot, Y., & Sollogoub, M. (2019). Bi(OTf) ₃ -mediated intramolecular epoxide opening for bicyclic azepane synthesis Journal of Carbohydrate Chemistry, 38(2), 139-149. https://doi.org/10.1080/07328303.2019.1581887

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title = " Bi(OTf) 3 -mediated intramolecular epoxide opening for bicyclic azepane synthesis ",

abstract = "While an epoxide on a sugar-derived aziridine studying was opened, an unexpected formation of bicyclic compounds was observed. The structure of these bicycles depended on the nature of the protecting group on the nitrogen atom of the aziridine. These compounds appeared to be weak glycosidase inhibitors.",

keywords = "Azasugar, Azepane, Glycosidase inhibitors",

author = "Sha Zhu and Tran, {Anh Tuan} and Yuki Hirokami and Geoffrey Gontard and Omar Khaled and Yongmin Zhang and Atsushi Kato and Yves Bl{\'e}riot and Matthieu Sollogoub",

note = "Publisher Copyright: {\textcopyright} 2019, {\textcopyright} 2019 Taylor & Francis Group, LLC.",

year = "2019",

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day = "12",

doi = "10.1080/07328303.2019.1581887",

language = "英語",

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Zhu, S, Tran, AT, Hirokami, Y, Gontard, G, Khaled, O, Zhang, Y, Kato, A, Blériot, Y & Sollogoub, M 2019, ' Bi(OTf) ₃ -mediated intramolecular epoxide opening for bicyclic azepane synthesis ', Journal of Carbohydrate Chemistry, vol. 38, no. 2, pp. 139-149. https://doi.org/10.1080/07328303.2019.1581887

Bi(OTf) ₃ -mediated intramolecular epoxide opening for bicyclic azepane synthesis . / Zhu, Sha; Tran, Anh Tuan; Hirokami, Yuki et al.
In: Journal of Carbohydrate Chemistry, Vol. 38, No. 2, 12.02.2019, p. 139-149.

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

TY - JOUR

T1 - Bi(OTf) 3 -mediated intramolecular epoxide opening for bicyclic azepane synthesis

AU - Zhu, Sha

AU - Tran, Anh Tuan

AU - Hirokami, Yuki

AU - Gontard, Geoffrey

AU - Khaled, Omar

AU - Zhang, Yongmin

AU - Kato, Atsushi

AU - Blériot, Yves

AU - Sollogoub, Matthieu

PY - 2019/2/12

Y1 - 2019/2/12

N2 - While an epoxide on a sugar-derived aziridine studying was opened, an unexpected formation of bicyclic compounds was observed. The structure of these bicycles depended on the nature of the protecting group on the nitrogen atom of the aziridine. These compounds appeared to be weak glycosidase inhibitors.

AB - While an epoxide on a sugar-derived aziridine studying was opened, an unexpected formation of bicyclic compounds was observed. The structure of these bicycles depended on the nature of the protecting group on the nitrogen atom of the aziridine. These compounds appeared to be weak glycosidase inhibitors.

KW - Azasugar

KW - Azepane

KW - Glycosidase inhibitors

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DO - 10.1080/07328303.2019.1581887

M3 - 学術論文

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EP - 149

JO - Journal of Carbohydrate Chemistry

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