Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate

Autor:	Hiroki Morita, Masaki Tsukamoto, Hiroshi Shirouzu
Rok vydání:	2014
Předmět:	Trimethylsilyl Pyrimidine Chemistry Organic Chemistry Biochemistry Medicinal chemistry chemistry.chemical_compound Perchlorate Drug Discovery Imidazole Thiazole Trifluoromethanesulfonate Nucleoside Oxazole
Zdroj:	Tetrahedron. 70:3635-3639
ISSN:	0040-4020
DOI:	10.1016/j.tet.2014.03.013
Popis:	Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5-phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::89c130356af8017802025f76e2a0db98 https://doi.org/10.1016/j.tet.2014.03.013 Zobrazit plný text záznamu Full Text from ScienceDirect