Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield; Synlett; Vol. 29, iss. 15
| Parent link: | Synlett Vol. 29, iss. 15.— 2018.— [P. 2043-2045] |
|---|---|
| Korporativní autor: | |
| Další autoři: | , , , |
| Shrnutí: | Title screen The 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. Режим доступа: по договору с организацией-держателем ресурса |
| Jazyk: | angličtina |
| Vydáno: |
2018
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| Témata: | |
| On-line přístup: | https://doi.org/10.1055/s-0037-1610648 |
| Médium: | Elektronický zdroj Kapitola |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=659371 |
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| 200 | 1 | |a Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield |f E. V. Stepanova [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: 12 tit.] | ||
| 330 | |a The 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 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Synlett | ||
| 463 | |t Vol. 29, iss. 15 |v [P. 2043-2045] |d 2018 | ||
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a mycobacterial arabinans | |
| 610 | 1 | |a oligosaccharides | |
| 610 | 1 | |a glycosylation | |
| 610 | 1 | |a orthoesters | |
| 610 | 1 | |a phenols | |
| 610 | 1 | |a reactivity pattern | |
| 610 | 1 | |a substituent effects | |
| 610 | 1 | |a solution structure | |
| 610 | 1 | |a олигосахариды | |
| 610 | 1 | |a гликозилирование | |
| 610 | 1 | |a ортоэфиры | |
| 610 | 1 | |a фенолы | |
| 701 | 1 | |a Stepanova |b E. V. |c chemist |c engineer of Tomsk Polytechnic University |f 1978- |g Elena Vladimirovna |3 (RuTPU)RU\TPU\pers\34245 | |
| 701 | 1 | |a Podvalniy |b N. M. | |
| 701 | 1 | |a Abronina |b P. I. |g Polina Igorevna | |
| 701 | 1 | |a Kononov |b L. O. |g Leonid Olegovich | |
| 712 | 0 | 2 | |a Национальный исследовательский Томский политехнический университет |b Исследовательская школа химических и биомедицинских технологий (ИШХБМТ) |c (2017- ) |3 (RuTPU)RU\TPU\col\23537 |
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| 856 | 4 | |u https://doi.org/10.1055/s-0037-1610648 | |
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