Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition

David J. Hotchkiss; Atsushi Kato; Barbara Odell; Timothy D.W. Claridge; George W.J. Fleet

doi:10.1016/j.tetasy.2007.02.001

Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition

David J. Hotchkiss, Atsushi Kato, Barbara Odell, Timothy D.W. Claridge, George W.J. Fleet^*

^*Corresponding author for this work

Hospital Pharmacy

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

22 Scopus citations

Abstract

The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of l-fucosidases and d-galactosidases is reported.

Original language	English
Pages (from-to)	500-512
Number of pages	13
Journal	Tetrahedron Asymmetry
Volume	18
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2007.02.001
State	Published - 2007/03/12

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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@article{e2ca5788064b49eb812dd5edb121931c,

title = "Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition",

abstract = "The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of l-fucosidases and d-galactosidases is reported.",

author = "Hotchkiss, {David J.} and Atsushi Kato and Barbara Odell and Claridge, {Timothy D.W.} and Fleet, {George W.J.}",

note = "Funding Information: A generous gift of 2-C-methyl- d -ribono-1,4-lactone is gratefully acknowledged. D.J.H. was supported by an EPSRC studentship.",

year = "2007",

month = mar,

day = "12",

doi = "10.1016/j.tetasy.2007.02.001",

language = "英語",

volume = "18",

pages = "500--512",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd.",

number = "4",

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TY - JOUR

T1 - Homochiral carbon branched piperidines from carbon branched sugar lactones

T2 - 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition

AU - Hotchkiss, David J.

AU - Kato, Atsushi

AU - Odell, Barbara

AU - Claridge, Timothy D.W.

AU - Fleet, George W.J.

N1 - Funding Information: A generous gift of 2-C-methyl- d -ribono-1,4-lactone is gratefully acknowledged. D.J.H. was supported by an EPSRC studentship.

PY - 2007/3/12

Y1 - 2007/3/12

N2 - The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of l-fucosidases and d-galactosidases is reported.

AB - The value of readily available 2-C-methyl aldonic acids in short syntheses of carbon branched piperidines containing quaternary centers is demonstrated. The effect of the introduction of a 4-C-methyl group into piperidine imino sugar inhibitors of l-fucosidases and d-galactosidases is reported.

UR - http://www.scopus.com/inward/record.url?scp=33947224481&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2007.02.001

DO - 10.1016/j.tetasy.2007.02.001

M3 - 学術論文

AN - SCOPUS:33947224481

SN - 0957-4166

VL - 18

SP - 500

EP - 512

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

Homochiral carbon branched piperidines from carbon branched sugar lactones: 4-C-methyl-deoxyfuconojirimycin (DFJ) and its enantiomer-removal of glycosidase inhibition

Abstract

ASJC Scopus subject areas

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