Targeted Synthesis of 3,3'-, 3,4'- and 3,6'-Phenylpropanoid Sucrose Esters

Wong Pooi Wen Kathy; Li Lin Ong; Surabhi Devaraj; Duc Thinh Khong; Zaher M.A. Judeh

doi:10.3390/molecules27020535

Targeted Synthesis of 3,3'-, 3,4'- and 3,6'-Phenylpropanoid Sucrose Esters

Wong Pooi Wen Kathy, Li Lin Ong, Surabhi Devaraj, Duc Thinh Khong, Zaher M.A. Judeh^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

In this study, we report on an orthogonal strategy for the precise synthesis of 3,3′-, 3,4′-, and 3,6′-phenylpropanoid sucrose esters (PSEs). The strategy relies on carefully selected protecting groups and deprotecting agents, taking into consideration the reactivity of the four free hydroxyl groups of the key starting material: Di-isopropylidene sucrose 2. The synthetic strategy is general, and potentially applies to the preparation of many natural and unnatural PSEs, especially those substituted at 3-, 3′-, 4- and 6′-positions of PSEs.

Original language	English
Article number	535
Journal	Molecules
Volume	27
Issue number	2
DOIs	https://doi.org/10.3390/molecules27020535
Publication status	Published - Jan 1 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022, MDPI. All rights reserved.

ASJC Scopus Subject Areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

Keywords

Antidiabetic compounds
Natural products
Orthogonal protection
Phenylpropanoid sucrose esters
Selective acylation of sugar

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10.3390/molecules27020535

Cite this

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abstract = "In this study, we report on an orthogonal strategy for the precise synthesis of 3,3′-, 3,4′-, and 3,6′-phenylpropanoid sucrose esters (PSEs). The strategy relies on carefully selected protecting groups and deprotecting agents, taking into consideration the reactivity of the four free hydroxyl groups of the key starting material: Di-isopropylidene sucrose 2. The synthetic strategy is general, and potentially applies to the preparation of many natural and unnatural PSEs, especially those substituted at 3-, 3′-, 4- and 6′-positions of PSEs.",

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AU - Kathy, Wong Pooi Wen

AU - Ong, Li Lin

AU - Devaraj, Surabhi

AU - Khong, Duc Thinh

AU - Judeh, Zaher M.A.

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AB - In this study, we report on an orthogonal strategy for the precise synthesis of 3,3′-, 3,4′-, and 3,6′-phenylpropanoid sucrose esters (PSEs). The strategy relies on carefully selected protecting groups and deprotecting agents, taking into consideration the reactivity of the four free hydroxyl groups of the key starting material: Di-isopropylidene sucrose 2. The synthetic strategy is general, and potentially applies to the preparation of many natural and unnatural PSEs, especially those substituted at 3-, 3′-, 4- and 6′-positions of PSEs.

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KW - Natural products

KW - Orthogonal protection

KW - Phenylpropanoid sucrose esters

KW - Selective acylation of sugar

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Targeted Synthesis of 3,3'-, 3,4'- and 3,6'-Phenylpropanoid Sucrose Esters

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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