Acceptor-influenced and donor-tuned base-promoted glycosylation
Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a mo...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2012-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.8.46 |
| _version_ | 1818854502030114816 |
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| author | Stephan Boettcher Martin Matwiejuk Joachim Thiem |
| author_facet | Stephan Boettcher Martin Matwiejuk Joachim Thiem |
| author_sort | Stephan Boettcher |
| collection | DOAJ |
| description | Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities. |
| first_indexed | 2024-12-19T07:53:43Z |
| format | Article |
| id | doaj.art-540e6dfa26bf47c79d37b11630f3274a |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T07:53:43Z |
| publishDate | 2012-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-540e6dfa26bf47c79d37b11630f3274a2022-12-21T20:30:04ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-03-018141342010.3762/bjoc.8.461860-5397-8-46Acceptor-influenced and donor-tuned base-promoted glycosylationStephan Boettcher0Martin Matwiejuk1Joachim Thiem2Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, GermanyGlycom A/S, c/o DTU, Building 201, Anker Engelunds Vej 1, DK-2800 Kgs. Lyngby, DenmarkDepartment of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, GermanyBase-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.https://doi.org/10.3762/bjoc.8.46glycosylationoxyanionreactivityregioselectivity |
| spellingShingle | Stephan Boettcher Martin Matwiejuk Joachim Thiem Acceptor-influenced and donor-tuned base-promoted glycosylation Beilstein Journal of Organic Chemistry glycosylation oxyanion reactivity regioselectivity |
| title | Acceptor-influenced and donor-tuned base-promoted glycosylation |
| title_full | Acceptor-influenced and donor-tuned base-promoted glycosylation |
| title_fullStr | Acceptor-influenced and donor-tuned base-promoted glycosylation |
| title_full_unstemmed | Acceptor-influenced and donor-tuned base-promoted glycosylation |
| title_short | Acceptor-influenced and donor-tuned base-promoted glycosylation |
| title_sort | acceptor influenced and donor tuned base promoted glycosylation |
| topic | glycosylation oxyanion reactivity regioselectivity |
| url | https://doi.org/10.3762/bjoc.8.46 |
| work_keys_str_mv | AT stephanboettcher acceptorinfluencedanddonortunedbasepromotedglycosylation AT martinmatwiejuk acceptorinfluencedanddonortunedbasepromotedglycosylation AT joachimthiem acceptorinfluencedanddonortunedbasepromotedglycosylation |