Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield

Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield

Dades bibliogràfiques
Parent link:	Synlett Vol. 29, iss. 15.— 2018.— [P. 2043-2045]
Autor corporatiu:	Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий (ИШХБМТ)
Altres autors:	Stepanova E. V. Elena Vladimirovna, Podvalniy N. M., Abronina P. I. Polina Igorevna, Kononov L. O. Leonid Olegovich
Sumari:	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
Idioma:	anglès
Publicat:	2018
Matèries:	электронный ресурс труды учёных ТПУ mycobacterial arabinans oligosaccharides glycosylation orthoesters phenols reactivity pattern substituent effects solution structure олигосахариды гликозилирование ортоэфиры фенолы
Accés en línia:	https://doi.org/10.1055/s-0037-1610648
Format:	Electrònic Capítol de llibre
KOHA link:	https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=659371

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