Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid

Tzenge Lien Shih; Shu Yu Yang

doi:10.3390/molecules17044498

Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid

Tzenge Lien Shih^*, Shu Yu Yang

^*Corresponding author for this work

Tamkang University

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

10 Scopus citations

Abstract

Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

Original language	English
Pages (from-to)	4498-4507
Number of pages	10
Journal	Molecules
Volume	17
Issue number	4
DOIs	https://doi.org/10.3390/molecules17044498
State	Published - 04 2012
Externally published	Yes

Keywords

Aminocyclitols
D-(-)-quinic acid
Epoxides
Glycosidase inhibitors
Regioselective ring opening

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10.3390/molecules17044498

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title = "Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid",

abstract = "Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.",

keywords = "Aminocyclitols, D-(-)-quinic acid, Epoxides, Glycosidase inhibitors, Regioselective ring opening",

author = "Shih, {Tzenge Lien} and Yang, {Shu Yu}",

year = "2012",

month = apr,

doi = "10.3390/molecules17044498",

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journal = "Molecules",

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AU - Shih, Tzenge Lien

AU - Yang, Shu Yu

PY - 2012/4

Y1 - 2012/4

N2 - Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

AB - Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.

KW - Aminocyclitols

KW - D-(-)-quinic acid

KW - Epoxides

KW - Glycosidase inhibitors

KW - Regioselective ring opening

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U2 - 10.3390/molecules17044498

DO - 10.3390/molecules17044498

M3 - 文章

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AN - SCOPUS:84860253225

SN - 1420-3049

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JO - Molecules

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ER -

Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid

Abstract

Keywords

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