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Communication | Special issue | Vol 52, No. 1, 2000, pp.141-146
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S54
Syntheis of Zeaxanthin- and Cryptoxanthin-β-D-glucopyranosides

Yumiko Yamano, Yoshitsugu Sakai, Satomi Yamashita, and Masayoshi Ito*

*Kobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan


β-Glucosidation of (3R)-3-hydroxy-β-ionone (6) was achieved in a reasonable yield by use of tetra-O-benzoyl-α-D-glucopyranosyl bromide (8c) as a glycosyl donor and silver triflate as an activator. The resulting glucoside (9) was transformed into the β-apo-12’-carotenal (18), which was condensed with the Wittig salt (19) or (20) to provide zeaxanthin-mono-β-D-glucopyranoside (3) or cryptoxanthin-β-D-glucopyranoside (4).