Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-beta-D-(glucopyranosyl-xylopyranosyl)-4',5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected D-glucose and D-xylose in aqueous solution as the key reactions.

Shingo Sato, Tomoyuki Koide

Graduate School of Science and Engineering, Yamagata University, Yamagata, Japan. shingo-s@yz.yamagata-u.ac.jp

Carbohydrate research 2010 Sep 3

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Vicenin-3 was synthesized from naringenin via a short five-step reaction, which included two regioselective direct C-glycosylations with d-glucose and d-xylose (yields: 22% and 30%, respectively) as the key reactions for a total yield of 4.4%. Vicenin-1 was also synthesized from phloroacetophenone via a 10-step reaction, including the same glycosylation described above, for a total yield of 2.7% with a vicenin-3 yield of 1.7%.

Citation

Shingo Sato, Tomoyuki Koide. Synthesis of vicenin-1 and 3, 6,8- and 8,6-di-C-beta-D-(glucopyranosyl-xylopyranosyl)-4',5,7-trihydroxyflavones using two direct C-glycosylations of naringenin and phloroacetophenone with unprotected D-glucose and D-xylose in aqueous solution as the key reactions. Carbohydrate research. 2010 Sep 3;345(13):1825-30