Реферат: The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The ‘matching’ in the donor–acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon—convenient building blocks for the preparation of neoglycoconjugates.

Библиографическая ссылка: Abronina P.I. , Fedina K.G. , Podvalnyy N.M. , Zinin A.I. , Chizhov A.O. , Kondakov N.N. , Torgov V.I. , Kononov L.O.
The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation
Carbohydrate Research. 2014. V.396. P.25-36. DOI: 10.1016/j.carres.2014.05.017 WOS Scopus OpenAlex

Идентификаторы БД:

Web of science:	WOS:000341874600004
Scopus:	2-s2.0-84905198850
OpenAlex:	W2058311033

Цитирование в БД:

БД	Цитирований
OpenAlex	43
Scopus	46
Web of science	44

Альметрики: