A General Synthesis of Iminosugars

Ciaran McDonnell; Linda Cronin; Julie L. O'Brien; Paul V. Murphy

doi:10.1021/jo035763u

A General Synthesis of Iminosugars

Ciaran McDonnell, Linda Cronin, Julie L. O'Brien, Paul V. Murphy

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

Abstract

1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-β-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

Original language	English
Pages (from-to)	3565-3568
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	69
Issue number	10
DOIs	https://doi.org/10.1021/jo035763u
Publication status	Published - 14 May 2004
Externally published	Yes

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title = "A General Synthesis of Iminosugars",

abstract = "1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-β-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.",

author = "Ciaran McDonnell and Linda Cronin and O'Brien, {Julie L.} and Murphy, {Paul V.}",

year = "2004",

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doi = "10.1021/jo035763u",

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volume = "69",

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journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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T1 - A General Synthesis of Iminosugars

AU - McDonnell, Ciaran

AU - Cronin, Linda

AU - O'Brien, Julie L.

AU - Murphy, Paul V.

PY - 2004/5/14

Y1 - 2004/5/14

N2 - 1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-β-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

AB - 1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-β-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

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SN - 0022-3263

VL - 69

SP - 3565

EP - 3568

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

A General Synthesis of Iminosugars

Abstract

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