Chemoenzymatic and biotransformation approaches for pharmaceutical applications
Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal q...
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iium-179512012-03-08T01:56:08Z http://irep.iium.edu.my/17951/ Chemoenzymatic and biotransformation approaches for pharmaceutical applications Omar, Muhammad Nor Q Science (General) Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal quantities of the disatereoisomeric epoxides 5/6 and 8/9 from 4 and 7 respectively. Other methods gave preferentially epoxides 5 or 8, except for treatment of 7 with tert-butyl hydroperoxide in the presence of titanium (IV) isopropoxide and L-(+)-diisopropyl tartrate which gave preferentially epoxide 9. Hydroxy-derivative 4, 7, 5, 6, 8 and 9 were converted into the fluoro-derivatives 16 - 21 by trimethylsilylation and treament with diethylaminosulphur trifluoride. Epoxides 6 and 9 were converted into 2-oxazolines 22 and 23 respectively by reaction with acetamide. 2009 Conference or Workshop Item NonPeerReviewed application/pdf en http://irep.iium.edu.my/17951/1/Planery_lecture_NSFT09.pdf application/pdf en http://irep.iium.edu.my/17951/2/Fermentation_technology.PDF application/pdf en http://irep.iium.edu.my/17951/3/NSFT_2009_planery.PDF application/pdf en http://irep.iium.edu.my/17951/4/NSFT_Plenary1.pdf Omar, Muhammad Nor (2009) Chemoenzymatic and biotransformation approaches for pharmaceutical applications. In: 2nd National Symposium on Fermentation Technology (NSFT 2009), 14-15 December 2009, MITC Ayer Keroh Malacca. (Unpublished) |
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Q Science (General) Omar, Muhammad Nor Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
description |
Methyl ricinoleate 4 and methyl 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoate 7 were subjected to epoxidation using mCPBA, or tert-butyl hydroperoxide in the presence of vanadyl acetylacetonate or titanium (IV) isopropoxide with D-(-)- or L-(+)-diisopropyl tartrate. Epoxidations using mCPBA gave equal quantities of the disatereoisomeric epoxides 5/6 and 8/9 from 4 and 7 respectively. Other methods gave preferentially epoxides 5 or 8, except for treatment of 7 with tert-butyl hydroperoxide in the presence of titanium (IV) isopropoxide and L-(+)-diisopropyl tartrate which gave preferentially epoxide 9. Hydroxy-derivative 4, 7, 5, 6, 8 and 9 were converted into the fluoro-derivatives 16 - 21 by trimethylsilylation and treament with diethylaminosulphur trifluoride. Epoxides 6 and 9 were converted into 2-oxazolines 22 and 23 respectively by reaction with acetamide. |
format |
Conference or Workshop Item |
author |
Omar, Muhammad Nor |
author_facet |
Omar, Muhammad Nor |
author_sort |
Omar, Muhammad Nor |
title |
Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
title_short |
Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
title_full |
Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
title_fullStr |
Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
title_full_unstemmed |
Chemoenzymatic and biotransformation approaches for pharmaceutical applications |
title_sort |
chemoenzymatic and biotransformation approaches for pharmaceutical applications |
publishDate |
2009 |
url |
http://irep.iium.edu.my/17951/ http://irep.iium.edu.my/17951/1/Planery_lecture_NSFT09.pdf http://irep.iium.edu.my/17951/2/Fermentation_technology.PDF http://irep.iium.edu.my/17951/3/NSFT_2009_planery.PDF http://irep.iium.edu.my/17951/4/NSFT_Plenary1.pdf |
first_indexed |
2023-09-18T20:27:00Z |
last_indexed |
2023-09-18T20:27:00Z |
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