Details
| Original language | English |
|---|---|
| Pages (from-to) | 3101-3115 |
| Number of pages | 15 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2005 |
| Issue number | 14 |
| Publication status | Published - 4 Jul 2005 |
| Externally published | Yes |
Abstract
A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-inositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C2- symmetric diacetoxyconduritol B key intermediate, followed by cis-dihydroxylation. Selective functionalization of axial and equatorial hydroxy groups allows the synthesis of symmetric inositol phosphates as well as unsymmetrical, enantiomerically pure inositol phosphates.
Keywords
- Asymmetric synthesis, Biocatalytic resolution, Inositol phosphates, Natural products, Phosphorylation, Protecting groups
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2005, No. 14, 04.07.2005, p. 3101-3115.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates(Part 1)
T2 - Via Symmetrical Conduritol B Derivatives
AU - Podeschwa, Michael A.L.
AU - Plettenburg, Oliver
AU - Altenbach, Hans Josef
PY - 2005/7/4
Y1 - 2005/7/4
N2 - A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-inositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C2- symmetric diacetoxyconduritol B key intermediate, followed by cis-dihydroxylation. Selective functionalization of axial and equatorial hydroxy groups allows the synthesis of symmetric inositol phosphates as well as unsymmetrical, enantiomerically pure inositol phosphates.
AB - A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-inositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C2- symmetric diacetoxyconduritol B key intermediate, followed by cis-dihydroxylation. Selective functionalization of axial and equatorial hydroxy groups allows the synthesis of symmetric inositol phosphates as well as unsymmetrical, enantiomerically pure inositol phosphates.
KW - Asymmetric synthesis
KW - Biocatalytic resolution
KW - Inositol phosphates
KW - Natural products
KW - Phosphorylation
KW - Protecting groups
UR - http://www.scopus.com/inward/record.url?scp=22544466436&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200400911
DO - 10.1002/ejoc.200400911
M3 - Article
AN - SCOPUS:22544466436
VL - 2005
SP - 3101
EP - 3115
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 14
ER -