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Regioselective Acyl...
Regioselective Acylation of 2 '- or 3 '-Hydroxyl Group in Salicin : Hemisynthesis of Acylated Salicins
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Chen, Shao (author)
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Yuxin, Pei (author)
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- Borg-Karlson, Anna-Karin (author)
- KTH,Organisk kemi
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Zhichao, Pei (author)
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(creator_code:org_t)
- 2014-09-15
- 2014
- English.
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In: Chemical Research in Chinese Universities. - : Springer Science and Business Media LLC. - 1005-9040 .- 2210-3171. ; 30:5, s. 774-777
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- Salicin-based phenolic glycosides(PGs) are important defensive substances against herbivore feeding and have good bioactivities. In this work, a novel approach for the synthesis of salicin-based PGs has been developed, by which PGs of 2'-O-acetylsalicin(5a), 3'-O-acetylsalicin(5b) and 3'-O-benzoylsalicin(5d) were hemisynthesized. The effects of acylation reagent, solvent and temperature on the regioselective acylation of 2'- or 3'-hydroxyl groups of salicin mediated by dibutyltin oxide were investigated. The optimal conditions under which the best regioselectivity reached for 5a-5d were discovered, respectively. Moreover, a tentative tin-oxygen coordination mechanism was put forward to explain the different regioselectivities shown under different conditions.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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