Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Bao Chen Qian; Akiko Kamori; Kyoko Kinami; Atsushi Kato; Yi Xian Li; George W.J. Fleet; Chu Yi Yu

doi:10.1039/c6ob00531d

Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Bao Chen Qian, Akiko Kamori, Kyoko Kinami, Atsushi Kato^*, Yi Xian Li, George W.J. Fleet, Chu Yi Yu

^*Corresponding author for this work

Hospital Pharmacy

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

16 Scopus citations

Abstract

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

Original language	English
Pages (from-to)	4488-4498
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	19
DOIs	https://doi.org/10.1039/c6ob00531d
State	Published - 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars",

abstract = "Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.",

author = "Qian, {Bao Chen} and Akiko Kamori and Kyoko Kinami and Atsushi Kato and Li, {Yi Xian} and Fleet, {George W.J.} and Yu, {Chu Yi}",

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year = "2016",

doi = "10.1039/c6ob00531d",

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volume = "14",

pages = "4488--4498",

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T2 - N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

AU - Qian, Bao Chen

AU - Kamori, Akiko

AU - Kinami, Kyoko

AU - Kato, Atsushi

AU - Li, Yi Xian

AU - Fleet, George W.J.

AU - Yu, Chu Yi

PY - 2016

Y1 - 2016

N2 - Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

AB - Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

UR - http://www.scopus.com/inward/record.url?scp=84970974343&partnerID=8YFLogxK

U2 - 10.1039/c6ob00531d

DO - 10.1039/c6ob00531d

M3 - 学術論文

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AN - SCOPUS:84970974343

SN - 1477-0520

VL - 14

SP - 4488

EP - 4498

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 19

ER -

Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Abstract

ASJC Scopus subject areas

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