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

Heterocycles

Volumn 52, Issue 1, 2000, Pages 141-146

  Yamano, Yumiko ^a   Sakai, Yoshitsugu ^a   Yamashita, Satomi ^a   Ito, Masayoshi ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY BETA IONONE; CRYPTOXANTHIN BETA DEXTRO GLUCOPYRANOSIDE; GLUCOPYRANOSIDE; IONONE DERIVATIVE; UNCLASSIFIED DRUG; ZEAXANTHIN BETA DEXTRO GLUCOPYRANOSIDE;

ARTICLE; COLUMN CHROMATOGRAPHY; HYDROLYSIS; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033957184     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s54     Document Type: Article

References (15)

1. A. Yokoyama, G. Sandmann, T. Hoshino, K. Adachi, M. Sakai, and Y. Shizuri, Tetraheron Lett., 1995, 36, 4901.
2. A. Yokoyama, Y. Shizuri, T. Hoshino, and G. Sandmann, Arch. Microbiol., 1996, 165, 342.
3. H. Pfander and M. Hodler, Helv. Chim. Acta, 1974, 57, 1641.
4. Y. Yamano, C. Tode, and M. Ito, J. Chem. Soc., Perkin Trans. 1, 1998, 2569.
5. Y. Ito and T. Ogawa, Tetrahedron Lett., 1988, 29, 1061.
6. J. Banoub and D. R. Bundle, Can. J. Chem., 1979, 57, 2091.
7. 11Na (M+Na), 809.294, found m/z 809.294.
8. 4 (Scheme 1) by Peterson reaction with TMS acetonitrile in the presence of LDA, following reduction with DIBALH [(all-E)-isomer: 48%; (9Z)-isomer: 24%], and subsequent deprotection (quant.) with 48% aqueous HF.
9. 5 75-80°C) was prepared (88%) from t-butylimine of acetaldehyde according to the literature; R. H. Schlessinger, M. A. Poss, S. Richardson, and P. Lin, Tetrahedron Lett., 1985, 26, 2391.
10. K. Bernhard, F. Kienzle, H. Mayer, and R. K. Müller, Helv. Chim. Acta, 1980, 63, 1473.
11. H. Pfander, A. Lachenmeier, and M. Hadorn, Helv. Chim. Acta, 1980, 63, 1377.
12. H. Pommer, Angew. Chem., 1960, 72, 811.
13. 15 However, other isomers of 3 and 4 could not be separable by HPLC.
14. G. Englert, K. Noack, E. A. Broger, E. Glinz, M. Vecchi, and R. Zell, Helv. Chim. Acta, 1991, 74, 969.
15. Y. Yamano, M. Yoshizawa, and M. Ito, J. Nutr. Sci. Vitaminol., 1999, 45, 49.