Scalable total synthesis of natural vanillin-derived glucoside ω-esters
| Parent link: | Carbohydrate Research Vol. 522.— 2022.— [108683, 7 p.] |
|---|---|
| Autor Corporativo: | |
| Outros Autores: | , , , |
| Resumo: | 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 |
| Idioma: | inglês |
| Publicado em: |
2022
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| Assuntos: | |
| Acesso em linha: | https://doi.org/10.1016/j.carres.2022.108683 |
| Formato: | Recurso Electrónico Capítulo de Livro |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=668680 |
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| 200 | 1 | |a Scalable total synthesis of natural vanillin-derived glucoside ω-esters |f D. L. Avetyan (Avetian), A. Shatskiy, M. D. Karkas, E. V. Stepanova | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: 57 tit.] | ||
| 330 | |a 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. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Carbohydrate Research | ||
| 463 | |t Vol. 522 |v [108683, 7 p.] |d 2022 | ||
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a total synthesis | |
| 610 | 1 | |a natural occurring | |
| 610 | 1 | |a glycosides | |
| 610 | 1 | |a vanilloloside | |
| 610 | 1 | |a calleryanin | |
| 610 | 1 | |a esters of glycosides | |
| 610 | 1 | |a plant metabolites | |
| 610 | 1 | |a синтез | |
| 610 | 1 | |a гликозиды | |
| 610 | 1 | |a сложные эфиры | |
| 610 | 1 | |a метаболиты | |
| 701 | 1 | |a Avetyan (Avetian) |b D. L. |c Chemical engineer |c Engineer of Tomsk Polytechnic University |f 1995- |g David Ludvigovich |3 (RuTPU)RU\TPU\pers\46600 | |
| 701 | 1 | |a Shatskiy |b A. |g Andrey | |
| 701 | 1 | |a Karkas |b M. D. |g Markus | |
| 701 | 1 | |a Stepanova |b E. V. |c chemist |c Associate Professor of Tomsk Polytechnic University, Candidate of Chemical Sciences |f 1988- |g Elena Vladimirovna |3 (RuTPU)RU\TPU\pers\34245 |9 17776 | |
| 712 | 0 | 2 | |a Национальный исследовательский Томский политехнический университет |c (2009- ) |b Исследовательская школа химических и биомедицинских технологий |b Лаборатория "Химическая инженерия и молекулярный дизайн" |9 26305 |
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