Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals |
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| Authors: | Peiran Chen Dalin Zhang |
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| Institution: | 1. Key Lab of Eco-Textile, The Ministry of Education, Donghua University, 2999 Renmin Road North, Songjiang District, Shanghai 201620, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, China |
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| Abstract: | By using Sm(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl–d-glucal or 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yield and high anomeric selectivity. It was found that under certain conditions, reaction of 3,4-di-O-acetyl-l-rhamnal with thiol leads to temperature-dependent formation of C-1-S and C-3-S product. A temperature-dependent profile of the yield of these two products is given. |
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| Keywords: | Sm(OTf)3 3 4 6-Tri-O-acetyl-d-glucal 3 4-Di-O-acetyl-l-rhamnal C-1-S and C-3-S glycopyranoside Ferrier rearrangement |
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