Scalable total synthesis of natural vanillin-derived glucoside ω-esters
| Parent link: | Carbohydrate Research Vol. 522.— 2022.— [108683, 7 p.] |
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| Corporate Author: | |
| Other Authors: | , , , |
| Summary: | Title screen The first total synthesis of vanilloloside, calleryanin, and a series of naturally occurring ω-esters of vanilloloside was realized through direct glycosylation of vanillin-based aglycones or late-stage derivatization of vanilloloside. All aglycones and their fragments were synthesized from vanillin as the sole aromatic precursor. Subsequently, these intermediates were used to construct various vanillin-derived glucoside ω-esters using a mild acidic deacetylation as the key synthetic step, providing the final products in the total yields of 10-50% and general purity of >95%. Additionally, the first operationally simple and sustainable synthesis of litseafoloside B was realized on large scale, avoiding the use of toxic solvents and reagents, providing an attractive alternative to isolation of this and other similar compounds from plant sources. Режим доступа: по договору с организацией-держателем ресурса |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://doi.org/10.1016/j.carres.2022.108683 |
| Format: | Electronic Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=668680 |