| 000 | 03792nlm1a2200505 4500 | ||
|---|---|---|---|
| 001 | 659030 | ||
| 005 | 20231030041615.0 | ||
| 035 | _a(RuTPU)RU\TPU\network\27345 | ||
| 090 | _a659030 | ||
| 100 | _a20181222a2018 k y0engy50 ba | ||
| 101 | 0 | _aeng | |
| 135 | _adrcn ---uucaa | ||
| 181 | 0 | _ai | |
| 182 | 0 | _ab | |
| 200 | 1 |
_aA new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides _fE. V. Stepanova [et al.] |
|
| 203 |
_aText _celectronic |
||
| 300 | _aTitle screen | ||
| 320 | _a[References: 39 tit.] | ||
| 330 | _aIn the present work we report that acetyl groups of per - acetylated aryl glycosides have different reactivity during the acidic deacetylation using HCl/EtOH in CHCl3, which leads to preferential deacetylation at O-3, O-4 and O-6. Thereby, the one-step preparation of 2-O-acetyl aryl glycosides with simple aglycon was accomplished for the first time. It was proved that the found reagent is to be general and unique for the preparation of series of 2-О-acetyl aryl glycosides. We have determined the influence of both carbohydrate moiety and the aglycon on the selectivity of deacetylation reaction by kinetic experiments. Using DFT/B3LYP/6-31G(d,p) and semi-empirical АМ1 methods we have found that the highest activation barrier is for 2-О-acetyl group. This completely explains the least reactivity of 2-О-acetyl group. | ||
| 333 | _aРежим доступа: по договору с организацией-держателем ресурса | ||
| 461 | _tCarbohydrate Research | ||
| 463 |
_tVol. 458-459 _v[P. 60-65] _d2018 |
||
| 610 | 1 | _aэлектронный ресурс | |
| 610 | 1 | _aтруды учёных ТПУ | |
| 610 | 1 | _aaryl glycosides | |
| 610 | 1 | _aregioselective deacetylation | |
| 610 | 1 | _areactivity | |
| 610 | 1 | _apartially acylated carbohydrates | |
| 610 | 1 | _atransition states modeling | |
| 610 | 1 | _aарилгликозиды | |
| 610 | 1 | _aреактивность | |
| 610 | 1 | _aуглеводы | |
| 610 | 1 | _aпереходные состояния | |
| 701 | 1 |
_aStepanova _bE. V. _cchemist _cengineer of Tomsk Polytechnic University _f1978- _gElena Vladimirovna _2stltpush _3(RuTPU)RU\TPU\pers\34245 |
|
| 701 | 1 |
_aNagornaya _bM. O. _cChemist _cAssistant of the Department of Tomsk Polytechnic University, Technician _f1990- _gMarina Olegovna _2stltpush _3(RuTPU)RU\TPU\pers\37479 |
|
| 701 | 1 |
_aFilimonov _bV. D. _cRussian chemist _cProfessor of the TPU _f1945- _gViktor Dmitrievich _2stltpush _3(RuTPU)RU\TPU\pers\26423 |
|
| 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 |
_aValiev _bR. R. _cchemist _cAssistant of Tomsk Polytechnic University _f1983- _gRashid Rinatovich _2stltpush _3(RuTPU)RU\TPU\pers\34114 |
|
| 701 | 1 |
_aDrozdova _bA. _gAnna |
|
| 701 | 1 |
_aCherepanov _bV. N. _gViktor Nikolaevich |
|
| 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 _bИнженерная школа новых производственных технологий _bНаучно-образовательный центр Н. М. Кижнера _h7872 _2stltpush _3(RuTPU)RU\TPU\col\23556 |
| 801 | 2 |
_aRU _b63413507 _c20181222 _gRCR |
|
| 856 | 4 | _uhttps://doi.org/10.1016/j.carres.2018.02.003 | |
| 942 | _cCF | ||