1,5-Anhydro-D-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin.

Peter Maier; Søren Møller Andersen; Inge Lundt

doi:10.1055/s-2006-926343

1,5-Anhydro-D-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin.

Peter Maier, Søren Møller Andersen, Inge Lundt

Department of Chemistry

Technical University of Denmark

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

Abstract

A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-D-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage.

Original language	English
Journal	Synthesis
Pages (from-to)	827-830
ISSN	0039-7881
DOIs	https://doi.org/10.1055/s-2006-926343
Publication status	Published - 2006

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title = "1,5-Anhydro-D-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin.",

abstract = "A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-D-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage.",

author = "Peter Maier and Andersen, {S{\o}ren M{\o}ller} and Inge Lundt",

year = "2006",

doi = "10.1055/s-2006-926343",

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journal = "Synthesis",

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T1 - 1,5-Anhydro-D-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin.

AU - Maier, Peter

AU - Andersen, Søren Møller

AU - Lundt, Inge

PY - 2006

Y1 - 2006

N2 - A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-D-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage.

AB - A novel six-step synthesis of 1-deoxymannojirimycin from 1,5-anhydro-D-fructose in 35% overall yield is reported. The key steps are nucleophilic piperidine ring formation and subsequent Lewis acid induced pyran ether cleavage.

U2 - 10.1055/s-2006-926343

DO - 10.1055/s-2006-926343

M3 - Journal article

SN - 0039-7881

SP - 827

EP - 830

JO - Synthesis

JF - Synthesis

ER -

1,5-Anhydro-D-fructose as Chiral Building Block: A Novel Approach to 1-Deoxymannojirimycin.

Abstract

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