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New approaches to analogs of α-linked galactosylceramides based on functionalized serinol Научная публикация

Журнал Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Вых. Данные Год: 2018, Том: 67, Номер: 12, Страницы: 2297-2306 Страниц : 10 DOI: 10.1007/s11172-018-2373-3
Авторы Jost U. 1 , Abronina P.I. 2 , Zinin A.I. 2 , Michalik D. 1,3 , Kragl U. 1 , Kondakov N.N. 2 , Chizov A.O. 2 , Torgov V.I. 2 , Kononov L.O. 2
Организации
1 Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3A, 18059, Rostock, Germany
2 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
3 Leibniz Institute for Catalysis (LIKAT), Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Реферат: New derivatives of serinol, 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol and 3-[4-(2-azidoethoxy)phenoxy]-2-phthalimidopropan-1-ol, were synthesized and tested as glycosyl acceptors in stereoselective 1,2-cis-galactosylation in the benzyl-free synthesis of analogs of α-linked galactosylceramides. It was found that NIS/AgOTf-promoted glycosylation of 3-[4-(2-chloroethoxy)benzyloxy]-2-phthalimidopropan-1-ol with ethyl 4,6-O-(di-tert-butylsilylene)-1-thio-β-D-galactoside resulted in both the expected α-linked diastereomeric glycosides and the product of iodination of the benzyl group of the aglycon. This process was avoided by using the corresponding galactosyl imidate under Et3SiOTf promotion to give exclusively α-linked diastereometic serinol glycosides.
Библиографическая ссылка: Jost U. , Abronina P.I. , Zinin A.I. , Michalik D. , Kragl U. , Kondakov N.N. , Chizov A.O. , Torgov V.I. , Kononov L.O.
New approaches to analogs of α-linked galactosylceramides based on functionalized serinol
Russian Chemical Bulletin. 2018. V.67. N12. P.2297-2306. DOI: 10.1007/s11172-018-2373-3 WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:000457425900026
Scopus: 2-s2.0-85061052805
OpenAlex: W2913275083
Цитирование в БД:
БД Цитирований
OpenAlex 4
Scopus 4
Web of science 4
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