Synthesis, Inhaltsverzeichnis Synthesis 2018; 50(02): 282-294DOI: 10.1055/s-0036-1590927 paper © Georg Thieme Verlag Stuttgart · New Yorkα-Selective Glycosylation of 3,6-O-o-Xylylene-Bridged Glucosyl Fluoride Atsushi Motoyama School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan eMail: hidetosh@kwansei.ac.jp , Tomoki Arai School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan eMail: hidetosh@kwansei.ac.jp , Kazutada Ikeuchi School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan eMail: hidetosh@kwansei.ac.jp , Kazuya Aki School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan eMail: hidetosh@kwansei.ac.jp , Shinnosuke Wakamori School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan eMail: hidetosh@kwansei.ac.jp , Hidetoshi Yamada * School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan eMail: hidetosh@kwansei.ac.jp› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Erratum zu diesem Artikel:α-Selective Glycosylation of 3,6-O-o-Xylylene-Bridged Glucosyl FluorideSynthesis 2018; 50(23): 4695-4695DOI: 10.1055/s-0037-1610841 Abstract A 1,2-cis-(α)-selective glycosylation has been developed. An ortho-xylylene group bridged between 3-O and 6-O of d-glucosyl fluoride, which straddles the β-face of the pyranose ring, hinders the approach of glycosyl acceptors from that face. The determination of the three-dimensional structure of the bridged glucosyl fluoride, the optimization process of the reaction conditions oriented toward kinetic control to realize the high α-selectivity, and the scope of the reaction are described. Key words Key wordsglycosylation - 1,2-cis-selectivity - kinetic control - conformation - o-xylylene bridge Volltext Referenzen References 1a Boons G.-J. Hale KJ. Organic Synthesis with Carbohydrates. Sheffield Academic Press; Sheffield: 2000 1b Demchenko AV. Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance. Wiley-VCH; Weinheim: 2008 2 Gridley JJ. Osborn HM. I. J. Chem. Soc., Perkin Trans. 1 2000; 1471 3a Banoub J. Bundle DR. Can. J. Chem. 1979; 57: 2091 3b Flitsh SL. Nature 2005; 437: 201 3c Guo J. Ye X.-S. 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