| 000 | 03526nlm1a2200409 4500 | ||
|---|---|---|---|
| 001 | 662821 | ||
| 005 | 20231030041833.0 | ||
| 035 | _a(RuTPU)RU\TPU\network\33979 | ||
| 035 | _aRU\TPU\network\33836 | ||
| 090 | _a662821 | ||
| 100 | _a20201109a2020 k y0engy50 ba | ||
| 101 | 0 | _aeng | |
| 135 | _adrcn ---uucaa | ||
| 181 | 0 | _ai | |
| 182 | 0 | _ab | |
| 200 | 1 |
_aDivergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides _fD. D. Fedorova, D. S. Nazarova, D. L. Avetyan (Avetian) [et al.] |
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| 203 |
_aText _celectronic |
||
| 300 | _aTitle screen | ||
| 330 | _aHerein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides—the selective deacetylation of the sugar moiety—was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5–17% overall yield, 90–95% purity), which are rare plant metabolites. | ||
| 333 | _aРежим доступа: по договору с организацией-держателем ресурса | ||
| 461 | _tJournal of Natural Products | ||
| 463 |
_tVol. 83, iss. 10 _v[P. 3173-3180] _d2020 |
||
| 610 | 1 | _aэлектронный ресурс | |
| 610 | 1 | _aтруды учёных ТПУ | |
| 610 | 1 | _aсинтез | |
| 701 | 1 |
_aFedorova _bD. D. _gDarjya |
|
| 701 | 1 |
_aNazarova _bD. S. _gDarjya |
|
| 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 |
_aBelyanin _bM. L. _corganic chemist _cAssociate Professor of Tomsk Polytechnic University, Candidate of chemical sciences _f1973- _gMaksim L'vovich _2stltpush _3(RuTPU)RU\TPU\pers\31268 |
|
| 701 | 1 |
_aKarkas _bM. D. _gMarkus |
|
| 701 | 1 |
_aStepanova _bE. V. _cchemist _cengineer of Tomsk Polytechnic University _f1978- _gElena Vladimirovna _2stltpush _3(RuTPU)RU\TPU\pers\34245 |
|
| 712 | 0 | 2 |
_aНациональный исследовательский Томский политехнический университет _bИсследовательская школа химических и биомедицинских технологий _c(2017- ) _h8120 _2stltpush _3(RuTPU)RU\TPU\col\23537 |
| 712 | 0 | 2 |
_aНациональный исследовательский Томский политехнический университет _bИнженерная школа новых производственных технологий _bНаучно-образовательный центр Н. М. Кижнера _h7872 _2stltpush _3(RuTPU)RU\TPU\col\23556 |
| 801 | 2 |
_aRU _b63413507 _c20201109 _gRCR |
|
| 856 | 4 | _uhttps://doi.org/10.1021/acs.jnatprod.0c00838 | |
| 942 | _cCF | ||