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Direct and stereoselective synthesis of β-D-mannosides using 4,6-O-benzylidene-protected mannosyl diethyl phosphite as a donor
| Title: | Direct and stereoselective synthesis of β-D-mannosides using 4,6-O-benzylidene-protected mannosyl diethyl phosphite as a donor |
| Authors: | Tsuda, Toshifumi1 Browse this author | | Arihara, Ryoichi2 Browse this author | | Sato, Shinya3 Browse this author | | Koshiba, Miyuki4 Browse this author | | Nakamura, Seiichi5 Browse this author | | Hashimoto, Shunichi6 Browse this author →KAKEN DB |
| Authors(alt): | 津田, 敏史1 | | 在原, 僚一2 | | 佐藤, 晋也3 | | 小柴, みゆき4 | | 中村, 精一5 | | 橋本, 俊一6 |
| Keywords: | 4,6-O-Benzylidene acetal | | Mannosyl diethyl phosphite | | β-Selective glycosidation |
| Issue Date: | 19-Sep-2005 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron |
| Volume: | 61 |
| Issue: | 45 |
| Start Page: | 10719 |
| End Page: | 10733 |
| Publisher DOI: | 10.1016/j.tet.2005.08.090 |
| Abstract: | A direct and practical method for the construction of β-mannosidic linkages is described. While β-selectivities in the TMSOTf-promoted glycosidation of 2,3,4,6-tetra-O-benzyl-D-mannosyl diethyl phosphite are found to be highly dependent on the reactivity of acceptor alcohols, 2,3-di-O-benzyl-4,6-O-benzylidene-D-mannosyl diethyl phosphite reacts with a wide range of acceptor alcohols in the presence of TMSOTf in CH2Cl2 at –45 °C to give β-mannosides in high yields with good to high β-selectivities. |
| Relation: | http://www.sciencedirect.com/science/journal/00404020 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/673 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 中村 精一
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