title: Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors.
abstract: Disaccharide nucleosides constitute an important group of naturally-occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O-glycosylation of nucleoside acceptors, such as adenosine, guanosine, thymidine, and cytidine, with glycosyl donors. Among the glycosyl donors tested, thioglycosides were found to give the corresponding disaccharide nucleosides in moderate to high chemical yields with the above nucleoside acceptors using p-toluenesulfenyl chloride (TolSCl) and silver triflate (AgOTf) as promoters. The interaction of these promoters with nucleoside acceptors was examined by (1)H NMR spectroscopic experiments.
authors: Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda 278-8510 (Japan), Fax: (+81) 4-7121-3670; Center for Technologies against Cancer, Tokyo University of Science, 2641 Yamazaki, Noda 278-8510 (Japan). shinaoki@rs.noda.tus.ac.jp.
authors: Shin
authors: S
authors: Aoki
authors: Taketo
authors: T
authors: Fukumoto
authors: Taiki
authors: T
authors: Itoh
authors: Masayuki
authors: M
authors: Kurihara
authors: Shigeto
authors: S
authors: Saito
authors: Shin-ya
authors: SY
authors: Komabiki
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D009705:Nucleosides; D013865:Thioglycosides
keywords: O-glycosylation; chemical glycosylation; disaccharide nucleosides; nucleosides; thioglycoside