New strategies for O- and C-glycosylation.

In part A, we have established an efficient iron-catalyzed decarboxylative C-glycosylation of glycals with β-keto acids via decarboxylative Ferrier rearrangement strategy. This approach provides a wide range of β-keto-functionalized 2,3-unsaturated C-glycosides in moderate to good yields. Good α-sel...

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Main Author: Tan, Hong Yee.
Other Authors: Liu Xuewei
Format: Theses and Dissertations
Language:English
Published: 2012
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Online Access:http://hdl.handle.net/10356/49504
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-495042023-02-28T23:55:46Z New strategies for O- and C-glycosylation. Tan, Hong Yee. Liu Xuewei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Carbohydrates In part A, we have established an efficient iron-catalyzed decarboxylative C-glycosylation of glycals with β-keto acids via decarboxylative Ferrier rearrangement strategy. This approach provides a wide range of β-keto-functionalized 2,3-unsaturated C-glycosides in moderate to good yields. Good α-selectivities are mainly observed with the use of D-galactals along with the bulkier β-keto acids bearing phenyl moieties. In part B, we have developed a highly regio- and stereoselective formation of β-O-arylpseudoglucals via palladium-catalyzed decarboxylative O-glycosylation strategy. This approach essentially relies on palladium’s decarboxylative feature to eliminate the carboxylate group located in C3 position, subsequently liberating phenolic nucleophile to attack onto the electron deficient anomeric position. This reaction system successfully provides a facile and direct entry to exclusive selectivity for β-O- glycosides. Master of Science 2012-05-21T04:12:32Z 2012-05-21T04:12:32Z 2012 2012 Thesis http://hdl.handle.net/10356/49504 en 70 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry::Carbohydrates
spellingShingle DRNTU::Science::Chemistry::Organic chemistry::Carbohydrates
Tan, Hong Yee.
New strategies for O- and C-glycosylation.
description In part A, we have established an efficient iron-catalyzed decarboxylative C-glycosylation of glycals with β-keto acids via decarboxylative Ferrier rearrangement strategy. This approach provides a wide range of β-keto-functionalized 2,3-unsaturated C-glycosides in moderate to good yields. Good α-selectivities are mainly observed with the use of D-galactals along with the bulkier β-keto acids bearing phenyl moieties. In part B, we have developed a highly regio- and stereoselective formation of β-O-arylpseudoglucals via palladium-catalyzed decarboxylative O-glycosylation strategy. This approach essentially relies on palladium’s decarboxylative feature to eliminate the carboxylate group located in C3 position, subsequently liberating phenolic nucleophile to attack onto the electron deficient anomeric position. This reaction system successfully provides a facile and direct entry to exclusive selectivity for β-O- glycosides.
author2 Liu Xuewei
author_facet Liu Xuewei
Tan, Hong Yee.
format Theses and Dissertations
author Tan, Hong Yee.
author_sort Tan, Hong Yee.
title New strategies for O- and C-glycosylation.
title_short New strategies for O- and C-glycosylation.
title_full New strategies for O- and C-glycosylation.
title_fullStr New strategies for O- and C-glycosylation.
title_full_unstemmed New strategies for O- and C-glycosylation.
title_sort new strategies for o- and c-glycosylation.
publishDate 2012
url http://hdl.handle.net/10356/49504
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