IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation

A facile method to convert thioglycosides to glycosyl fluorides with Ipy2BF4 (py = pyridine) is presented. Alternatively, activation of thioglycosides with Ipy2BF4 in the presence of acids and glycosyl acceptors led to glycosylation reactions. Perbenzylated (armed) glycosyl donors yielded predominan...

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Bibliographic Details
Published in:European Journal of Organic Chemistry
Main Authors: Huang, Kuo-Ting, Winssinger, Nicolas
Format: Article in Journal/Newspaper
Language:English
Published: 2007
Subjects:
Carbohydrates
Glycosylation
Thioglycosides
Iodine
IPY
Online Access:https://archive-ouverte.unige.ch/unige:24446
id ftunivgeneve:oai:unige.ch:aou:unige:24446
record_format openpolar
spelling ftunivgeneve:oai:unige.ch:aou:unige:24446 2023-10-01T03:57:02+02:00 IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation Huang, Kuo-Ting Winssinger, Nicolas 2007 https://archive-ouverte.unige.ch/unige:24446 eng eng info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200700038 https://archive-ouverte.unige.ch/unige:24446 unige:24446 info:eu-repo/semantics/restrictedAccess ISSN: 1099-0690 European journal of organic chemistry, vol. 2007, no. 12 (2007) p. 1887-1890 Carbohydrates Glycosylation Thioglycosides Iodine info:eu-repo/semantics/article Text Article scientifique info:eu-repo/semantics/publishedVersion 2007 ftunivgeneve https://doi.org/10.1002/ejoc.200700038 2023-09-07T07:05:05Z A facile method to convert thioglycosides to glycosyl fluorides with Ipy2BF4 (py = pyridine) is presented. Alternatively, activation of thioglycosides with Ipy2BF4 in the presence of acids and glycosyl acceptors led to glycosylation reactions. Perbenzylated (armed) glycosyl donors yielded predominantly the β-anomeric product. This methodology is compatible with one-pot sequential glycosylation. Article in Journal/Newspaper IPY Université de Genève: Archive ouverte UNIGE European Journal of Organic Chemistry 2007 12 1887 1890
institution Open Polar
collection Université de Genève: Archive ouverte UNIGE
op_collection_id ftunivgeneve
language English
topic Carbohydrates
Glycosylation
Thioglycosides
Iodine
spellingShingle Carbohydrates
Glycosylation
Thioglycosides
Iodine
Huang, Kuo-Ting
Winssinger, Nicolas
IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation
topic_facet Carbohydrates
Glycosylation
Thioglycosides
Iodine
description A facile method to convert thioglycosides to glycosyl fluorides with Ipy2BF4 (py = pyridine) is presented. Alternatively, activation of thioglycosides with Ipy2BF4 in the presence of acids and glycosyl acceptors led to glycosylation reactions. Perbenzylated (armed) glycosyl donors yielded predominantly the β-anomeric product. This methodology is compatible with one-pot sequential glycosylation.
format Article in Journal/Newspaper
author Huang, Kuo-Ting
Winssinger, Nicolas
author_facet Huang, Kuo-Ting
Winssinger, Nicolas
author_sort Huang, Kuo-Ting
title IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation
title_short IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation
title_full IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation
title_fullStr IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation
title_full_unstemmed IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation
title_sort ipy 2 bf 4 -mediated glycosylation and glycosyl fluoride formation
publishDate 2007
url https://archive-ouverte.unige.ch/unige:24446
genre IPY
genre_facet IPY
op_source ISSN: 1099-0690
European journal of organic chemistry, vol. 2007, no. 12 (2007) p. 1887-1890
op_relation info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200700038
https://archive-ouverte.unige.ch/unige:24446
unige:24446
op_rights info:eu-repo/semantics/restrictedAccess
op_doi https://doi.org/10.1002/ejoc.200700038
container_title European Journal of Organic Chemistry
container_volume 2007
container_issue 12
container_start_page 1887
op_container_end_page 1890
_version_ 1778527948405473280

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