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Direct and stereoselective synthesis of β-D-mannosides using 4,6-O-benzylidene-protected mannosyl diethyl phosphite as a donor

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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)

Submitter: 中村 精一

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