Synthesis of zeaxanthin- and cryptoxanthin-beta-D-glucopyranosides

Authors
Yamano, Y Sakai, Y Yamashita, S Ito, M
Citation
Y. Yamano et al., Synthesis of zeaxanthin- and cryptoxanthin-beta-D-glucopyranosides, HETEROCYCLE, 52(1), 2000, pp. 141-146
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
1
Year of publication
2000
Pages
141 - 146
Database
ISI
SICI code
0385-5414(20000101)52:1<141:SOZAC>2.0.ZU;2-4
Abstract
beta-Glucosidation of (3R)-3-hydroxy-beta-ionone (6) was achieved in a reas onable yield by use of tetra-O-benzoyl-alpha-D-glucopyranosyl bromide (8 c) as a glycosyl donor and silver triflate as an activator. The resulting glu coside (9) was transformed into the beta-apo-12'-carotenal (18), which was condensed with the Wittig salt (19) or (20) to provide zeaxanthin-mono-beta -D-glucopyranoside (3) or cryptoxanthin-beta-D-glucopyranoside (4).