Convenient use of ortho-formylphenyl thioglycoside for regioselective conjugation with glycosyl acceptors towards regioselective 1,2-cis-glycosylation |
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| Authors: | Hirofumi Dohi Ryota Komai Hidetoshi Sakai Haruka Komuro Yoshihiro Nishida |
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| Institution: | 1. Department of Bioresource Science, Graduate School of Horticulture;2. Molecular Chirality Research Center hdohi@faculty.chiba-u.jp;4. Department of Nanoscience, Graduate School of Advanced Integration of Science, Chiba University, Chiba, Japan;5. Molecular Chirality Research Center;6. Department of Nanoscience, Graduate School of Advanced Integration of Science, Chiba University, Chiba, Japan |
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| Abstract: | A facile methodology is proposed for regioselective conjugation between glycosyl donors and acceptors towards the development of regioselective 1,2-cis-glycosylation method. ortho-Formylphenyl 1-thio-β-d-galactopyranoside was regioselectively tethered to methyl α-d-glucopyranoside under acidic condition to furnish an 4,6-O-arylidene acetal-linked conjugate. This conjugate can be readily converted to an ether-linked 4-O- or 6-O-derivative by regioselective cleavage of the acetal ring. In the glycosylation reaction, the ether-linked 4-OH conjugate was found to show excellent 1,2-cis selectivity via an intramolecular 1,9-transfer. |
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| Keywords: | intramolecular glycosylation thioglycosides stereoselective glycosylation regioselective reaction |
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