Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study
Both enantiomers of 1-(1,3-dithian-2-yl)-2-propanol (5) 1-(1,3-dithiolan-2-yl)-2-propanol (6), and halogenated derivatives of 5 was obtained by microbial reductions and lipase catalyzed esterifications. (2S)-1-(1,3-dithian-2-yl)-3-chloro-2-propanol and (2R)-(1,3-dithian-2-yl)-3-chloro-2-propanol wer...
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ftntnutrondheimi:oai:ntnuopen.ntnu.no:11250/228354 2023-05-15T14:15:39+02:00 Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study Seland, John Georg Norges teknisk-naturvitenskapelige universitet, Fakultet for naturvitenskap og teknologi, Institutt for kjemi 2000 application/pdf http://hdl.handle.net/11250/228354 eng eng Fakultet for naturvitenskap og teknologi Dr. ingeniøravhandling, 0809-103X; 2000:112 122540 urn:isbn:82-7984-141-5 http://hdl.handle.net/11250/228354 Doctoral thesis 2000 ftntnutrondheimi 2023-02-08T23:43:36Z Both enantiomers of 1-(1,3-dithian-2-yl)-2-propanol (5) 1-(1,3-dithiolan-2-yl)-2-propanol (6), and halogenated derivatives of 5 was obtained by microbial reductions and lipase catalyzed esterifications. (2S)-1-(1,3-dithian-2-yl)-3-chloro-2-propanol and (2R)-(1,3-dithian-2-yl)-3-chloro-2-propanol were converted to both enantiomers of 2-(1,3-dithian-2-ylmethyl)oxirane. 3-(1,3-Dithiane-2-yl)-3-buten-2-one (3) was biologically transformed to (S)-3-(1,3-dithian-2-yl)-2butanone. Efficient methods have been developed for lipase catalyzed kinetic resolution of series of 1-(2-thienyl-alkanoles using lipase B from Candida antartica. 1-(2-Thienyl)-ethanone (13) was reduced to (S)-1-(2-theinyl)-ethanol with fermenting cells and various cell-preparations of Geotrichum candidum. Cyclohexyl 4-bromo-3hydroxybutanoate (24) and benzyl 4-bromo-3-hydroxybutanoate (25) was tested in lipase catalyzed kinetic resolutions with limited success. Ethyl 3-oxobutanoate and halogenated derivatives (21-23) were reduced enantioselectively by Geotrichum candidum. This revealed that G.candidum seems to contain at least two dehydrogenases with opposite stereoselectivity. (1E)-1-Phenylhexa-1,5-dien-3-ol (26) was resolved by transeterifications using lipase B from Candida antartica and vinyl acrylate. Seperation of the enantiomers by column chromatography, subsequent chemical esterification of the unreacted enantiomer and ring closing metathesis yielded both enantiomers of the biologcally active compound Goniothalamin. dr.ing. dr.ing. Doctoral or Postdoctoral Thesis antartic* NTNU Open Archive (Norwegian University of Science and Technology) |
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NTNU Open Archive (Norwegian University of Science and Technology) |
op_collection_id |
ftntnutrondheimi |
language |
English |
description |
Both enantiomers of 1-(1,3-dithian-2-yl)-2-propanol (5) 1-(1,3-dithiolan-2-yl)-2-propanol (6), and halogenated derivatives of 5 was obtained by microbial reductions and lipase catalyzed esterifications. (2S)-1-(1,3-dithian-2-yl)-3-chloro-2-propanol and (2R)-(1,3-dithian-2-yl)-3-chloro-2-propanol were converted to both enantiomers of 2-(1,3-dithian-2-ylmethyl)oxirane. 3-(1,3-Dithiane-2-yl)-3-buten-2-one (3) was biologically transformed to (S)-3-(1,3-dithian-2-yl)-2butanone. Efficient methods have been developed for lipase catalyzed kinetic resolution of series of 1-(2-thienyl-alkanoles using lipase B from Candida antartica. 1-(2-Thienyl)-ethanone (13) was reduced to (S)-1-(2-theinyl)-ethanol with fermenting cells and various cell-preparations of Geotrichum candidum. Cyclohexyl 4-bromo-3hydroxybutanoate (24) and benzyl 4-bromo-3-hydroxybutanoate (25) was tested in lipase catalyzed kinetic resolutions with limited success. Ethyl 3-oxobutanoate and halogenated derivatives (21-23) were reduced enantioselectively by Geotrichum candidum. This revealed that G.candidum seems to contain at least two dehydrogenases with opposite stereoselectivity. (1E)-1-Phenylhexa-1,5-dien-3-ol (26) was resolved by transeterifications using lipase B from Candida antartica and vinyl acrylate. Seperation of the enantiomers by column chromatography, subsequent chemical esterification of the unreacted enantiomer and ring closing metathesis yielded both enantiomers of the biologcally active compound Goniothalamin. dr.ing. dr.ing. |
author2 |
Norges teknisk-naturvitenskapelige universitet, Fakultet for naturvitenskap og teknologi, Institutt for kjemi |
format |
Doctoral or Postdoctoral Thesis |
author |
Seland, John Georg |
spellingShingle |
Seland, John Georg Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
author_facet |
Seland, John Georg |
author_sort |
Seland, John Georg |
title |
Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
title_short |
Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
title_full |
Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
title_fullStr |
Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
title_full_unstemmed |
Diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
title_sort |
diffusion in heterogeneous polymer systems : a nuclear magnetic resonance study |
publisher |
Fakultet for naturvitenskap og teknologi |
publishDate |
2000 |
url |
http://hdl.handle.net/11250/228354 |
genre |
antartic* |
genre_facet |
antartic* |
op_relation |
Dr. ingeniøravhandling, 0809-103X; 2000:112 122540 urn:isbn:82-7984-141-5 http://hdl.handle.net/11250/228354 |
_version_ |
1766287968818954240 |