Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies
n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga’s reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2 BF 4 ), gives good yields of glycosyl fluorides when HF–pyridine complex...
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crcansciencepubl:10.1139/cjc-2012-0285 2023-12-17T10:32:32+01:00 Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies Fraser-Reid, Bert Lopez, J. Cristobal Bernal-Albert, Paloma Gomez, Ana M. Uriel, Clara Ventura, Juan 2013 http://dx.doi.org/10.1139/cjc-2012-0285 http://www.nrcresearchpress.com/doi/full-xml/10.1139/cjc-2012-0285 http://www.nrcresearchpress.com/doi/pdf/10.1139/cjc-2012-0285 en eng Canadian Science Publishing http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining Canadian Journal of Chemistry volume 91, issue 1, page 51-65 ISSN 0008-4042 1480-3291 Organic Chemistry General Chemistry Catalysis journal-article 2013 crcansciencepubl https://doi.org/10.1139/cjc-2012-0285 2023-11-19T13:39:40Z n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga’s reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2 BF 4 ), gives good yields of glycosyl fluorides when HF–pyridine complex is used as an additional fluoride source. NPOEs can be activated either by a combination of electrophilic iodonium (Barluenga’s reagent) and HBF 4 or by the action of HF–pyridine complex. The ensuing glycosyl fluorides form a semiorthogonal pair of glycosyl donors when confronted with NPGs. Article in Journal/Newspaper IPY Canadian Science Publishing (via Crossref) Canadian Journal of Chemistry 91 1 51 65 |
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Canadian Science Publishing (via Crossref) |
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crcansciencepubl |
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English |
topic |
Organic Chemistry General Chemistry Catalysis |
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Organic Chemistry General Chemistry Catalysis Fraser-Reid, Bert Lopez, J. Cristobal Bernal-Albert, Paloma Gomez, Ana M. Uriel, Clara Ventura, Juan Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies |
topic_facet |
Organic Chemistry General Chemistry Catalysis |
description |
n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga’s reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2 BF 4 ), gives good yields of glycosyl fluorides when HF–pyridine complex is used as an additional fluoride source. NPOEs can be activated either by a combination of electrophilic iodonium (Barluenga’s reagent) and HBF 4 or by the action of HF–pyridine complex. The ensuing glycosyl fluorides form a semiorthogonal pair of glycosyl donors when confronted with NPGs. |
format |
Article in Journal/Newspaper |
author |
Fraser-Reid, Bert Lopez, J. Cristobal Bernal-Albert, Paloma Gomez, Ana M. Uriel, Clara Ventura, Juan |
author_facet |
Fraser-Reid, Bert Lopez, J. Cristobal Bernal-Albert, Paloma Gomez, Ana M. Uriel, Clara Ventura, Juan |
author_sort |
Fraser-Reid, Bert |
title |
Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies |
title_short |
Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies |
title_full |
Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies |
title_fullStr |
Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies |
title_full_unstemmed |
Glycosyl fluorides from n -pentenyl-related glycosyl donors — Application to glycosylation strategies |
title_sort |
glycosyl fluorides from n -pentenyl-related glycosyl donors — application to glycosylation strategies |
publisher |
Canadian Science Publishing |
publishDate |
2013 |
url |
http://dx.doi.org/10.1139/cjc-2012-0285 http://www.nrcresearchpress.com/doi/full-xml/10.1139/cjc-2012-0285 http://www.nrcresearchpress.com/doi/pdf/10.1139/cjc-2012-0285 |
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IPY |
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IPY |
op_source |
Canadian Journal of Chemistry volume 91, issue 1, page 51-65 ISSN 0008-4042 1480-3291 |
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http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining |
op_doi |
https://doi.org/10.1139/cjc-2012-0285 |
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Canadian Journal of Chemistry |
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91 |
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1 |
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51 |
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65 |
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1785586305997996032 |