The first total synthesis of telephiose A |
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Authors: | Ken-ichi Sato Koudai Sakai Keiko Tsushima Shoji Akai |
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Institution: | Laboratory of Organic Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan |
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Abstract: | The first total synthesis of telephiose A (1), a novel trisaccharide ester having two acetyl groups and two benzoyl groups, was achieved by using glucosyl donor 6 and disaccharide acceptor 12. The crucial key step was the stereoselective construction of the β-d-glucosidic linkage featuring the neighboring group participation of the 2-O-N-phenylcarbamoyl group (of donor 6), which can be selectively deprotected in the presence of acetyl and benzoyl groups. Donor 6 was prepared from d-glucose in eight steps (33% yield), whereas acceptor 12 was prepared from sucrose in six steps (35% yield). Precursors 6 and 12 were reacted in subsequent reactions (five steps) to afford 1 in 22% yield. |
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Keywords: | Telephiose Total synthesis Oligosaccharide esters N-Phenylcarbamoyl group |
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