Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed S(N)2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols |
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| Authors: | Tsuchiya Hitoshi Asakura Noriaki Ikeda Yasunori Yamada Hidetoshi |
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| Affiliation: | School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan |
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| Abstract: | A highly stereoselective synthesis of C-vinyl furanosides through the SN2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent SN2 intramolecular debenzyloxyation-cycloetherification reaction at the C-3 position. |
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| Keywords: | C-Vinyl furanosides 1,2-Dideoxy-hept-1-enitols SN2 intramolecular debenzyloxyation-cycloetherification Diphenylammonium trifluoromethanesulfonate |
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