Synthesis of flavonoid 2-deoxyglucosides via the Mitsunobu reaction |
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| Authors: | Ziyi Han Zhiwei Zheng Li Cai Dandan Zhou Changsheng Li Qiang Sui Shuai Liu Qi Gao |
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| Institution: | 1. China State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, China;2. Department of Chemistry, University of South Carolina Lancaster, 476 Hubbard Drive, Lancaster, South Carolina 29720, USA;3. GenChim Testing (Shanghai) Co., Ltd, 526 3rd East Fute Rd, Waigaoqiao Pilot Free Trade Zone, Shanghai 200131, China |
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| Abstract: | The Mitsunobu reaction of flavonoids and 3,4,6-tri-O-acetyl-2-deoxy-d-glucopyranose or 3,4,6-tri-O-benzyl-2-deoxy-d-glucopyranose is a very effective method for the stereoselective synthesis of flavonoid 2-deoxyglucosides. Since there is no C2 substituent on the sugar moieties, the observed α- or β-stereoselectivity was mainly controlled by the (acetyl or benzyl) protecting groups. Possible mechanistic insights are offered to explain the dual stereoselectivity. |
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| Keywords: | Flavonoid glycosides Synthesis Mitsunobu reaction Glycosylation Stereoselectivity |
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