Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/162140
Title: An orthogonal approach for the precise synthesis of phenylpropanoid sucrose esters
Authors: Ong, Li Lin
Wong, Kathy Pooi Wen
Raj, Surhabi Deva
Khong, Duc Thinh
Panda, Parthasarathi
Santoso, Mardi
Judeh, Zaher M. A.
Keywords: Engineering::Chemical engineering
Issue Date: 2022
Source: Ong, L. L., Wong, K. P. W., Raj, S. D., Khong, D. T., Panda, P., Santoso, M. & Judeh, Z. M. A. (2022). An orthogonal approach for the precise synthesis of phenylpropanoid sucrose esters. New Journal of Chemistry, 46(20), 9710-9717. https://dx.doi.org/10.1039/d2nj00881e
Journal: New Journal of Chemistry
Abstract: Phenylpropanoid sucrose esters (PSEs) are plant-derived metabolites that exist widely in medicinal plants and possess important bioactivities. Their precise synthesis is challenging due to the distinct and diverse substitution patterns at the sugar framework, and it is scarcely reported. Orthogonal protection/deprotection strategies for disaccharides are more complex and less developed than those for monosaccharides. We disclose a precise synthesis of PSEs starting from 2,1′:4,6-di-O-diisopropylidene sucrose 7via an orthogonal protection/deprotection and selective cinnamoylation strategy. We demonstrate the strategy for the synthesis of several PSEs cinnamoylated at the O-3 and O-4′ positions of diisopropylidene sucrose 7. The strategy is enabled by a carefully selected and synergistic set of protecting groups and deprotecting agents under the optimized conditions. It potentially gives access to the ∼150 reported PSEs and opens the door for the custom synthesis of unnatural PSEs for industrial applications. The reported work also presents a viable strategy for the general orthogonal protection/deprotection of disaccharides for the precise synthesis of other classes of phenylpropanoid esters and related compounds.
URI: https://hdl.handle.net/10356/162140
ISSN: 1144-0546
DOI: 10.1039/d2nj00881e
Rights: © 2022 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:IGS Journal Articles
SCBE Journal Articles

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