Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

Manuel Zoidl; Bernhard Müller; Ana Torvisco Gomez; Christina Tysoe; Mohamed Benazza; Aloysius Siriwardena; Stephen Withers; Tanja Wrodnigg

doi:10.1016/j.bmcl.2014.03.069

Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

Manuel Zoidl, Bernhard Müller, Ana Torvisco Gomez, Christina Tysoe, Mohamed Benazza, Aloysius Siriwardena^*, Stephen Withers, Tanja Wrodnigg^*

^*Korrespondierende/r Autor/-in für diese Arbeit

Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

Abstract

A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.

Originalsprache	englisch
Seiten (von - bis)	2777-2780
Fachzeitschrift	Bioorganic & Medicinal Chemistry Letters
Jahrgang	24
DOIs	https://doi.org/10.1016/j.bmcl.2014.03.069
Publikationsstatus	Veröffentlicht - 2014

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Basic - Fundamental (Grundlagenforschung)

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10.1016/j.bmcl.2014.03.069

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title = "Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy",

abstract = "A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.",

author = "Manuel Zoidl and Bernhard M{\"u}ller and {Torvisco Gomez}, Ana and Christina Tysoe and Mohamed Benazza and Aloysius Siriwardena and Stephen Withers and Tanja Wrodnigg",

year = "2014",

doi = "10.1016/j.bmcl.2014.03.069",

language = "English",

volume = "24",

pages = "2777--2780",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "1464-3405",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

AU - Zoidl, Manuel

AU - Müller, Bernhard

AU - Torvisco Gomez, Ana

AU - Tysoe, Christina

AU - Benazza, Mohamed

AU - Siriwardena, Aloysius

AU - Withers, Stephen

AU - Wrodnigg, Tanja

PY - 2014

Y1 - 2014

N2 - A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.

AB - A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.

U2 - 10.1016/j.bmcl.2014.03.069

DO - 10.1016/j.bmcl.2014.03.069

M3 - Article

SN - 1464-3405

VL - 24

SP - 2777

EP - 2780

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

ER -

Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

Abstract

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