| 000 | 03427nlm1a2200505 4500 | ||
|---|---|---|---|
| 001 | 668680 | ||
| 005 | 20231030042156.0 | ||
| 035 | _a(RuTPU)RU\TPU\network\39917 | ||
| 035 | _aRU\TPU\network\27916 | ||
| 090 | _a668680 | ||
| 100 | _a20230117a2022 k y0engy50 ba | ||
| 101 | 0 | _aeng | |
| 135 | _adrcn ---uucaa | ||
| 181 | 0 | _ai | |
| 182 | 0 | _ab | |
| 200 | 1 |
_aScalable total synthesis of natural vanillin-derived glucoside ω-esters _fD. L. Avetyan (Avetian), A. Shatskiy, M. D. Karkas, E. V. Stepanova |
|
| 203 |
_aText _celectronic |
||
| 300 | _aTitle screen | ||
| 320 | _a[References: 57 tit.] | ||
| 330 | _aThe 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 | _aРежим доступа: по договору с организацией-держателем ресурса | ||
| 461 | _tCarbohydrate Research | ||
| 463 |
_tVol. 522 _v[108683, 7 p.] _d2022 |
||
| 610 | 1 | _aэлектронный ресурс | |
| 610 | 1 | _aтруды учёных ТПУ | |
| 610 | 1 | _atotal synthesis | |
| 610 | 1 | _anatural occurring | |
| 610 | 1 | _aglycosides | |
| 610 | 1 | _avanilloloside | |
| 610 | 1 | _acalleryanin | |
| 610 | 1 | _aesters of glycosides | |
| 610 | 1 | _aplant metabolites | |
| 610 | 1 | _aсинтез | |
| 610 | 1 | _aгликозиды | |
| 610 | 1 | _aсложные эфиры | |
| 610 | 1 | _aметаболиты | |
| 701 | 1 |
_aAvetyan (Avetian) _bD. L. _cChemical engineer _cEngineer of Tomsk Polytechnic University _f1995- _gDavid Ludvigovich _2stltpush _3(RuTPU)RU\TPU\pers\46600 |
|
| 701 | 1 |
_aShatskiy _bA. _gAndrey |
|
| 701 | 1 |
_aKarkas _bM. D. _gMarkus |
|
| 701 | 1 |
_aStepanova _bE. V. _cchemist _cAssociate Professor of Tomsk Polytechnic University, Candidate of Chemical Sciences _f1988- _gElena Vladimirovna _2stltpush _3(RuTPU)RU\TPU\pers\34245 |
|
| 712 | 0 | 2 |
_aНациональный исследовательский Томский политехнический университет _bИсследовательская школа химических и биомедицинских технологий (ИШХБМТ) _c(2017- ) _h8120 _2stltpush _3(RuTPU)RU\TPU\col\23537 |
| 712 | 0 | 2 |
_aНациональный исследовательский Томский политехнический университет _bИсследовательская школа химических и биомедицинских технологий _bЛаборатория "Химическая инженерия и молекулярный дизайн" _h9100 _2stltpush _3(RuTPU)RU\TPU\col\27978 |
| 801 | 2 |
_aRU _b63413507 _c20230117 _gRCR |
|
| 856 | 4 | _uhttps://doi.org/10.1016/j.carres.2022.108683 | |
| 942 | _cCF | ||