Details
| Original language | English |
|---|---|
| Pages (from-to) | 1919-1929 |
| Number of pages | 11 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 1 |
| Issue number | 11 |
| Early online date | 30 Apr 2003 |
| Publication status | Published - 2003 |
| Externally published | Yes |
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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic and Biomolecular Chemistry, Vol. 1, No. 11, 2003, p. 1919-1929.
Research output: Contribution to journal › Article › Research › peer review
}
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.
UR - http://www.scopus.com/inward/record.url?scp=0037588943&partnerID=8YFLogxK
U2 - 10.1039/b302622a
DO - 10.1039/b302622a
M3 - Article
C2 - 12945774
AN - SCOPUS:0037588943
VL - 1
SP - 1919
EP - 1929
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 11
ER -