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Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline Научная публикация

Журнал Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215
Вых. Данные Год: 2024, Том: 536, Номер статьи : 109040, Страниц : DOI: 10.1016/j.carres.2024.109040
Авторы Pertel Sergey S. 1 , Kakayan Elena S. 1 , Zinin Alexander I. 2 , Kononov Leonid O. 2
Организации
1 V.I. Vernadsky Crimean Federal University, Vernadsky Ave., 4, 295007, Simferopol, Russian Federation
2 N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp., 47, 119991, Moscow, Russian Federation

Реферат: A synthesis of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline – a previously unknown 2-alkoxy glyco-[2,1-d]-2-oxazoline derivative with d-galacto configuration was carried out. Glycosylating activity of the obtained galactooxazoline has been studied and it has been shown that in the presence of a weak protic acid, such as sym-collidinium triflate, this substance exhibits properties of a reactive and 1,2-trans-stereoselective glycosyl donor. The homopolymerization reaction of oxazoline derivatives of sugars has been found to proceed under the same conditions, leading to the formation of pseudo-oligosaccharide products. It has been found that this undesirable side reaction could be suppressed by changing the acid catalyst concentration, resulting in the development of efficient methods for the synthesis of glycoside and oligosaccharide derivatives of β-d-galactosamine using the synthesized 2-(2,2,2-trichloroethoxy)-2-oxazoline glycosyl donor under very mild conditions.
Библиографическая ссылка: Pertel S.S. , Kakayan E.S. , Zinin A.I. , Kononov L.O.
Synthesis and study of the glycosyl-donor properties of 2-(2,2,2-trichloroethoxy)-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-galactopyrano)-[2,1-d]-2-oxazoline
Carbohydrate Research. 2024. V.536. 109040 . DOI: 10.1016/j.carres.2024.109040 WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:001164312200001
Scopus: 2-s2.0-85182624229
OpenAlex: W4390705053
Цитирование в БД:
БД Цитирований
OpenAlex 2
Scopus 3
Web of science 2
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