Synthesis of Arbutin Derivative with a Kojic Acid Moiety

Jun-ichi KADOKAWA*, Toshimitsu NISHIKURA, Hideyuki TAGAYA and Naohiko FUKUOKA

Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University; Yonezawa-shi 992-8510 Japan
Chemipro Kasei Kaisha, Ltd.; Chuo-ku, Kobe-shi 650-0044 Japan

This paper describes synthesis of new hybrid compound 3 consisting of arbutin (1) and kojic acid (2). The compound was synthesized in four step reactions from 1. At first, phenolic hydroxy group of 1 was protected, and then tosyl group was introduced at position 6, giving rise to the electrophile-type arbutin derivative 5. Then, the nucleophilic substitution of 2 with 5 successfully took place in the presence of DBU in DMF solvent to produce the hybrid compound 6. Finally, the deprotection of the benzyl group was carried out by the catalytic hydrogenation to give the desired compound 3. The analytical data of the compound fully supported the structure of 3.

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