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A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-D-glycosyl diphenyl phosphates as glycosyl donors

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タイトル: A highly stereoselective construction of 1,2-trans-β-glycosidic linkages capitalizing on 2-azido-2-deoxy-D-glycosyl diphenyl phosphates as glycosyl donors
著者: Tsuda, Toshifumi 著作を一覧する
Nakamura, Seiichi 著作を一覧する
Hashimoto, Shunichi 著作を一覧する
キーワード: 2-Azido-2-deoxyglycopyranosyl diphenyl phosphate
β-Selective glycosidation
α-Nitrilium ion
発行日: 2004年10月 1日
出版者: Elsevier
誌名: Tetrahedron
巻: 60
号: 47
開始ページ: 10711
終了ページ: 10737
出版社 DOI: 10.1016/j.tet.2004.08.076
抄録: The scope of TMSOTf-promoted glycosidation of 2-azido-2-deoxyglycopyranosyl diphenyl phosphates is investigated. The 3,4,6-tri-O-benzyl-protected glucosyl and galactosyl donors and the 4,6-O-benzylidene-protected galactosyl donor each react with a range of acceptor alcohols in the presence of a stoichiometric amount of TMSOTf in propionitrile at -78 °C to afford 1,2-trans-β-linked disaccharides in high yields with α:β ratios ranging from 9:91 to 1:>99, regardless of the anomeric composition of the donor used. The use of propionitrile as a solvent at -78 °C has proven to be among the best choice for the highest levels of β-selectivity reported to date for this type of glycosidation. A plausible reaction mechanism, which features a large equilibrium preference for α-glycosyl-nitrilium ions over β-nitrilium ions, is proposed based on byproducts formed through their intermediacy and accounts for the observed excellent β-selectivities.
Relation (URI): http://www.sciencedirect.com/science/journal/00404020
資料タイプ: article (author version)
URI: http://hdl.handle.net/2115/614
出現コレクション:雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

提供者: 中村 精一

 

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