Synergistic solvent effect in 1,2-cis-glycoside formation |
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| Authors: | Akihiro Ishiwata Yuichi Munemura Yukishige Ito |
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| Affiliation: | a RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
b CREST, JST, Kawaguchi 332-1102, Japan |
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| Abstract: | Construction of three continuous 1,2-cis-α-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d7) groups. It enabled facile evaluation of yield and stereoselectivity with 1H NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the α-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glcα1→2Glcα1→3Glcα1→3Man (Glc3Man1), which was achieved in 86% overall stereoselectivity. |
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| Keywords: | 1,2-cis-Glycosylation α-Glucoside Stereoselective Solvent effect |
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