Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone

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  • Bergische Universität Wuppertal
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OriginalspracheEnglisch
Seiten (von - bis)1919-1929
Seitenumfang11
FachzeitschriftOrganic and Biomolecular Chemistry
Jahrgang1
Ausgabenummer11
Frühes Online-Datum30 Apr. 2003
PublikationsstatusVeröffentlicht - 2003
Extern publiziertJa

Abstract

A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.

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Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone. / Podeschwa, Michael A.L.; Plettenburg, Oliver; Altenbach, Hans Josef.
in: Organic and Biomolecular Chemistry, Jahrgang 1, Nr. 11, 2003, S. 1919-1929.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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title = "Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone",
abstract = "A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.",
author = "Podeschwa, {Michael A.L.} and Oliver Plettenburg and Altenbach, {Hans Josef}",
note = "Funding Information: We are grateful to the Bayer AG Company for supporting this project in many aspects, especially for preparing the HR-MS spectra. We also thank in particular Dr. W. Schrader and Mrs. Blumenthal (Max-Planck Institut f{\"u}r Kohlenforschung) for mass spectra analysis. We thank Dr S. Adelt and G. Dallmann for purification of the inositol phosphates.",
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publisher = "Royal Society of Chemistry",
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Download

TY - JOUR

T1 - Stereoselective synthesis of several azido/amino- and diazido/diamino-myo-inositols and their phosphates from p-benzoquinone

AU - Podeschwa, Michael A.L.

AU - Plettenburg, Oliver

AU - Altenbach, Hans Josef

N1 - Funding Information: We are grateful to the Bayer AG Company for supporting this project in many aspects, especially for preparing the HR-MS spectra. We also thank in particular Dr. W. Schrader and Mrs. Blumenthal (Max-Planck Institut für Kohlenforschung) for mass spectra analysis. We thank Dr S. Adelt and G. Dallmann for purification of the inositol phosphates.

PY - 2003

Y1 - 2003

N2 - A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.

AB - A practical route is described for the preparation of azido-myo-inositols, amino-myo-inositols and azido-conduritol B derivatives. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol B derivative. Selective introduction of nitrogen-containing functional groups in four of the six possible positions in the cyclitol moiety is followed by further functionalization to yield the target compounds.

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U2 - 10.1039/b302622a

DO - 10.1039/b302622a

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VL - 1

SP - 1919

EP - 1929

JO - Organic and Biomolecular Chemistry

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SN - 1477-0520

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