| 000 | 02772nlm1a2200505 4500 | ||
|---|---|---|---|
| 001 | 659371 | ||
| 005 | 20231030041626.0 | ||
| 035 | _a(RuTPU)RU\TPU\network\27921 | ||
| 090 | _a659371 | ||
| 100 | _a20190214a2018 k y0engy50 ba | ||
| 101 | 0 | _aeng | |
| 102 | _aDE | ||
| 135 | _adrcn ---uucaa | ||
| 181 | 0 | _ai | |
| 182 | 0 | _ab | |
| 200 | 1 |
_aLength Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield _fE. V. Stepanova [et al.] |
|
| 203 |
_aText _celectronic |
||
| 300 | _aTitle screen | ||
| 320 | _a[References: 12 tit.] | ||
| 330 | _aThe outcome of the nucleophilic opening of 3-O-benzoyl-β-d-arabinofuranose 1,2,5-orthobenzoate with 4-(ω-chloroalkoxy)phenols (SnCl4, CH2Cl2, -25 °C) unusually strongly depends on the length of the methylene chain of the nucleophile. The presence of one extra methylene group in the molecule of 4-(3-chloropropoxy)phenol [as compared to 4-(2-chloroetoxy)phenol] results in four-fold reduction in the reaction time and five-fold increase in the yield of a selectively protected monosaccharide glycoside with a hydroxy group at C-5, which is a valuable building block for the synthesis of oligoarabinofuranosides related to mycobacterial arabinans. Possible reasons and consequences of this finding are discussed. | ||
| 333 | _aРежим доступа: по договору с организацией-держателем ресурса | ||
| 461 | _tSynlett | ||
| 463 |
_tVol. 29, iss. 15 _v[P. 2043-2045] _d2018 |
||
| 610 | 1 | _aэлектронный ресурс | |
| 610 | 1 | _aтруды учёных ТПУ | |
| 610 | 1 | _amycobacterial arabinans | |
| 610 | 1 | _aoligosaccharides | |
| 610 | 1 | _aglycosylation | |
| 610 | 1 | _aorthoesters | |
| 610 | 1 | _aphenols | |
| 610 | 1 | _areactivity pattern | |
| 610 | 1 | _asubstituent effects | |
| 610 | 1 | _asolution structure | |
| 610 | 1 | _aолигосахариды | |
| 610 | 1 | _aгликозилирование | |
| 610 | 1 | _aортоэфиры | |
| 610 | 1 | _aфенолы | |
| 701 | 1 |
_aStepanova _bE. V. _cchemist _cengineer of Tomsk Polytechnic University _f1978- _gElena Vladimirovna _2stltpush _3(RuTPU)RU\TPU\pers\34245 |
|
| 701 | 1 |
_aPodvalniy _bN. M. |
|
| 701 | 1 |
_aAbronina _bP. I. _gPolina Igorevna |
|
| 701 | 1 |
_aKononov _bL. O. _gLeonid Olegovich |
|
| 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 |
| 801 | 2 |
_aRU _b63413507 _c20190214 _gRCR |
|
| 856 | 4 | _uhttps://doi.org/10.1055/s-0037-1610648 | |
| 942 | _cCF | ||