New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition

Ying Zhou; Paul V. Murphy

doi:10.1021/ol8014495

New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition

Ying Zhou, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

75 Citations (Scopus)

Abstract

(Chemical Equation Presented) The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

Original language	English
Pages (from-to)	3777-3780
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	17
DOIs	https://doi.org/10.1021/ol8014495
Publication status	Published - 2008
Externally published	Yes

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title = "New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition",

abstract = "(Chemical Equation Presented) The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.",

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AU - Zhou, Ying

AU - Murphy, Paul V.

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

AB - (Chemical Equation Presented) The synthesis of 1-deoxynojirimycin (DNJ) derivatives is described from D-glucono-δ-lactone. The DNJ derivatives were obtained via a sequence that included a stereoselective intramolecular Huisgen reaction, decomposition to an aziridine, and its subsequent reaction with a nucleophile. Minimization of allylic strain in the transition state accounts for the stereoselectivity of the cycloaddition reaction.

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U2 - 10.1021/ol8014495

DO - 10.1021/ol8014495

M3 - Article

SN - 1523-7060

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SP - 3777

EP - 3780

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

New access to 1-deoxynojirimycin derivatives via azide-alkene cycloaddition

Abstract

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